Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones

ABSTRACT

Compounds of the formula ##STR1## wherein R 1  is hydrogen or C 1  -C 4  alkyl; R 2  is hydrogen, C 1  -C 4  alkyl or ##STR2## wherein R a  is C 1  -C 4  alkyl; R 1  and R 2  together are alkylene having 3 to 6 carbon atoms; R 3  is hydrogen or C 1  -C 4  alkyl; R 4  is hydrogen or C 1  -C 4  alkyl; R 5  is hydrogen or C 1  -C 4  alkyl; R 6  is hydrogen or C 1  -C 4  alkyl; R 7  is hydrogen or 3-C 1  -C 4  alkoxy; and R 8  is (1) hydrogen; (2) halogen; (3) C 1  -C 4  alkyl; (4) C 1  -C 4  alkoxy; (5) OCF 3  ; (6) cyano; (7) nitro; (8) C 1  -C 4  haloalkyl; (9) R b  SO n  -- wherein n is the integer 0, 1 or 2; and R b  is (a) C 1  -C 4  alkyl; (b) C 1  -C 4  alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR c  R d  wherein R c  and R d  independently are hydrogen or C 1  -C 4  alkyl; (11) R e  C(O)-- wherein R e  is C 1  -C 4  alkyl or C 1  -C 4  alkoxy; or (12) SO 2  NR c  R d  wherein R c  and R d  are as defined, their use as herbicides and herbicidal compositions containing the compounds.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a divisional of Application Ser. No. 880,370, Jun. 30, 1986, now U.S. Pat. No. 4,780,127, which is a continuation-in-part application of Application Ser. No. 802,135, filed Nov. 29, 1985, now abandoned; which in turn is a continuation-in-part of Application Ser. No. 683,900, filed Dec. 20, 1984, now abandoned.

Applications specifically incorporate by reference the contents of the above listed U.S. patent applications.

BACKGROUND OF THE INVENTION

Compounds having the structural formula ##STR3## wherein X can be alkyl, n can be 0, 1, or 2, and R₁ can be phenyl or substituted phenyl are described in Japanese Patent Application 84632-1974 as being intermediates for the preparation of herbicidal compounds of the formula ##STR4## wherein R₁, X, and n are as defined above and R₂ is alkyl, alkenyl, or alkynyl. Specifically taught herbicidal compounds of this latter group are those where n is 2, X is 5,5-dimethyl, R₂ is allyl and R₁ is phenyl, 4-chlorophenyl or 4-methoxyphenyl.

The precursor intermediates for these three specifically taught compounds have no or almost no herbicidal activity.

DESCRIPTION OF THE INVENTION

Embodiment A of this invention relates to certain novel 2-(2-substituted benzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of this embodiment have the following structural formula ##STR5## wherein

R and R¹ are hydrogen, C₁ -C₄ alkyl, preferably methyl or isopropyl, R^(a) OC(O)--, where R^(a) is C₁ -C₄ alkyl; most preferably R and R¹ are hydrogen;

R² is chlorine, bromine, iodine or C₁ -C₄ alkoxy, preferably methoxy; most preferably R₂ is chlorine, bromine or methoxy;

R³ R⁴ and R⁵ independently are hydrogen or an aliphatic group, preferably: (1) hydrogen; (2) halogen, preferably chlorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein R^(b) is C₁ -C₄ alkyl, preferably methyl, C₁ -C₄ haloalkyl, phenyl, benzyl, --NR^(d) R^(e) wherein R^(d) and R^(e) independently are hydrogen or C₁ -C₄ alkyl; and n is the integer 0, 1 or 2, preferably 2; ##STR6## wherein R^(c) is C₁ -C₄ alkyl and R^(j) is hydrogen or C₁ -C₄ alkyl, preferably methyl; (11) R^(f) C(O) wherein R^(f) is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy; (12) --NR^(g) R^(h) wherein R^(g) and R^(h) independently are hydrogen or C₁ -C₄ alkyl; or less preferably (13) R³ and R⁴ together can form a ring structure with two adjacent carbon atoms of the phenyl ring.

R³ and R⁴ can also be (14) C₃ -C₅ alkenyloxy (thio) optionally substituted, preferably with halogen or (15) C₃ -C₅ alkynyloxy (thio), optionally substituted, preferably with halogen.

Most preferably, R³ is chlorine, hydrogen, dimethylamino or methoxy. Preferably, R⁴ is hydrogen, chlorine, nitro, SO₂ CH₃, SO₂ N(CH₃)₂ or tirfluoromethyl. Preferably, R⁵ is hydrogen.

Embodiment A' of this invention is an herbicidal composition comprising an herbicidally active 2-benzoyl-1,3-cyclohexanedione and an inert carrier therefor. Preferably, the 2-position of the benzoyl moiety is substituted with chlorine, bromine, iodine or C₁ -C₄ alkoxy; more preferably chlorine, bromine or methoxy; most preferably chlorine. The 5-position of the 1,3-cyclohexanedione moiety can be substituted with one or two C₁ -C₄ alkyl groups, preferably methyl, although such a substitution is not preferred.

The compounds of Embodiment A of this invention can have the following four structural formulae because of tautomerism: ##STR7## wherein R, R¹, R², R³, R⁴ and R⁵ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR8## wherein R, R¹, R², R³, R⁴ and R⁵ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals, e.g. lithium, sodium, and potassium, alkaline earth metals, e.g. barium, magnesium, calcium and strontium or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

In the above description of the compounds of this invention, alkyl and alkoxy include both straight and branched configurations; for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

Embodiment B of this invention relates to certain novel 2-(2-substituted benzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of this embodiment have the following structural formula ##STR9## wherein

R¹⁰ is C₁ -C₆ alkyl, preferably C₁ -C₄ more preferably methyl;

R¹¹ is hydrogen or C₁ -C₆ alkyl, preferably C₁ -C₄, more preferably methyl or ##STR10## wherein

R^(a) is C₁ -C₄ alkyl or R¹⁰ and R¹¹ together are alkylene having 3 to 6 carbon atoms, most preferably R¹¹ is hydrogen or methyl;

R¹² is chlorine, bromine, iodine, fluorine or C₁ -C₄ alkoxy, preferably methoxy; most preferably R¹² is chlorine, bromine or methoxy;

R¹³ and R¹⁴ independently are (1) hydrogen or an aliphatic group, preferably hydrogen; (2) halogen, preferably, fluorine, chlorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ aliphatic alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein R^(b) is C₁ -C₄ alkyl, preferably methyl, C₁ -C₄ haloalkyl, phenyl benzyl, --NR^(d) R^(e) wherein R^(d) and R^(e) independently are hydrogen or C₁ -C₄ alkyl; and n is the integer 0, 1 or 2, preferably 2; ##STR11## wherein

R^(c) is C₁ -C₄ alkyl and R^(j) is hydrogen or C₁ -C₄ alkyl, preferably methyl; (11) R^(f) C(O) wherein R^(f) is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy; (12) --NR^(g) R^(h) wherein R^(g) and R^(h) independently are hydrogen or C₁ -C₄ alkyl; (13) C₁ -C₄ alkylthio or less preferably (14) R¹³ and R¹⁴ together can form a ring structure with two adjacent carbon atoms of the phenyl ring to which they are attached or less preferably (15) R¹³ and R¹⁴ are the groups phenoxy or substituted phenoxy wherein the substituent is halogen or halomethyl or both;

R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are independently the same or different and are selected from the group consisting of hydrogen, C₁ -C₆ alkyl, preferably C₁ -C₄ alkyl, more preferably methyl, most preferably hydrogen or methyl, and their salts;

provided, however, that R¹⁵ and R¹⁶ together may form a substituted or unsubstituted alkylene ring of 2-5 carbon atoms, the preferred substituent being 1 or 2 methyl groups.

More preferably, R¹³ is chlorine, hydrogen, methyl alkylthio or methoxy. Preferably R¹⁴ is hydrogen, chlorine, nitro, trifluoromethyl, or R^(b) SO_(n) wherein R^(b) is C₁ -C₄ alkyl, preferably methyl and n is the integer 0, 1 or 2, preferably 2.

The compounds of Embodiment B of this invention can have the following four structural formulae because of tautomerism: ##STR12## wherein R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR13## wherein R¹⁰, R¹¹, R¹², R¹³, R¹⁴, Rhu 15, R¹⁶, R¹⁷ and R¹⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium, alkaline earth metals, e.g. barium, magnesium, calcium and strontium, or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

The term "aliphatic group" is used form Embodiments A and B herein in a broad sense to cover a large class of organic groups characterized by being derived from (1) an acylic (open-chain structure) of the paraffin, olefin and acetylene hydrocarbon series and their derivatives or (2) alicyclic compounds. The aliphatic group can have from 1 to 10 carbon atoms.

The term "aromatic group" is used for Embodiments A and B herein in a broad sense to distinguish from the aliphatic group and includes a group derived from (1) compounds having 6 to 20 carbon atoms and characterized by the presence of at least one benzene ring, including monocyclic, bicyclic and polycyclic hydrocarbons and their derivatives and (2) heterocyclic compounds having 5 to 19 carbon atoms which are similar in structure and are characterized by having an unsaturated ring structure containing at least one atom other than carbon such as nitrogen, sulfur and oxygen and derivatives of these heterocyclic compounds.

In the above description of the compounds of this invention alkyl and alkoxy include both straight and branched configurations; for example, methyl, ethyl, n-propyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

Embodiment C of this invention relates to certain novel 2-(2'-cyanobenzoyl)cyclohexane-1,3-diones as herbicides. The compounds of of this embodiment have the following structural formula ##STR14## wherein

R²¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R²¹ is hydrogen or methyl;

R²² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR15## wherein R^(a) is C₁ -C₄ alkyl, most preferably R²² is hydrogen or methyl; or R²¹ and R²² together are alkylene having 3 to 6 carbon atoms;

R²³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R²³ is hydrogen or methyl;

R²⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R²⁴ is hydrogen or methyl;

R²⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R²⁵ is hydrogen or methyl;

R²⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R²⁶ is hydrogen;

R²⁷ and R²⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferbly methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R²⁷ is not attached to the 6-position.

Preferably, R²⁷ is in the 3-position. Most preferably R²⁷ is hydrogen and R²⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this embodiment can have the following four structural formulae because of tautomerism: ##STR16## wherein R²¹ R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷ and R²⁸ are as defined above.

The circled portion on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the follow four resonance forms: ##STR17## wherein R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷ and R²⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

Embodiment D of this invention relates to 2-(2-nitrobenzoyl)-1,3-cyclohexanediones and their use as herbicides.

The compounds have a nitro substitution in the 2-position of the phenyl moiety of their compounds. The nitro substitution imparts excpetional herbicidal activity to the compounds of this invention.

Embodiment D' of this invention is an herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione and an inert carrier therefor. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzyol moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment D have the following structural formula ##STR18## wherein

R³¹ is hydrogen or C₁ -C₄ alkly, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R³¹ is hydrogen or methyl;

R³² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR19## wherein

R^(a) is C₁ -C₄ alkyl, most preferably R³² pl is hydrogen or methyl; or

R³¹ and R³² together are alkylene having 3 to 6 carbon atoms;

R³³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³³ is hydrogen or methyl;

R³⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³⁴ is hydrogen or methyl;

R³⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R³⁵ is hydrogen or methyl;

R³⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R³⁶ is hydrogen;

R³⁷ and R³⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ R^(c) and R^(d) are as defined, with the proviso that R³⁷ is not attached to the 6-position.

Preferably, R³⁷ is in the 3-position. Most preferably R³⁷ is hydrogen or C₁ -C₄ alkoxy and R³⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The terms "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chlorine, bromine, iodine or fluorine.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR20## wherein R³¹, R³², R³³, R³⁴, R³⁶, R³⁷ and R³⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR21## wherein R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷ and R³⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium or organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substituent is an aliphatic or aromatic group.

Embodiment E of this invention relates to 2-(2-benzoyl-1,3-cyclohexanediones and their use as herbicides.

Embodiment E' of this invention is an herbicidal composition comprising an herbicidally active 2-(2-C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl or C₁ -C₄ alkylsulfonyl benzoyl)-1,3-cyclohexanedione and an inert carrier therefor. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment E have the structural formula ##STR22## wherein

n is the integer 0, 1 or 2, preferably 2;

R⁴⁰ is C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁴¹ is hydrogen or methyl;

R⁴² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR23## wherein R^(a) is C₁ -C₄ alkyl, most preferably R⁴² is hydrogen or methyl; or

R⁴¹ and R⁴² together are alkylene having 3 to 6 carbon atoms;

R⁴³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴³ is hydrogen or methyl;

R⁴⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴⁴ is hydrogen or methyl;

R⁴⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁴⁵ is hydrogen or methyl;

R⁴⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁴⁶ is hydrogen;

R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁴⁷ is not attached to the 6-position.

Preferably, R⁴⁷ is in the 3-position. Most preferably R⁴⁷ is hydrogen or 3-chlorine and R⁴⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

The term "C₁ -C₄ " alkyl includes methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The term "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chloro, bromo, iodo or fluoro.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR24## wherein n, R⁴⁰, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁸ are as defined above.

The circles proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR25## wherein n, R⁴⁰, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals e.g. lithium, sodium, and potassium, organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substitutent is an aliphatic or aromatic group.

Embodiment F of this invention relates to 2-(2-alkylbenzoyl)-1,3-cyclohexanediones and their use as herbicides.

Embodiment F' of this invention is an herbicidal composition comprising an herbicidally active 2-benzoyl-1,3-cyclohexanedione and an inert carrier therefor wherein the 2-position of the benzoyl moiety is substituted with C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, optionally substituted with halogen, more preferably methyl or trifluoromethyl and the 4-position preferably is substituted with an electron withdrawing group, such as halogen, cyano, trifluoromethyl or nitro. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moiety can be substituted, preferably with the groups hereinafter recited. More preferably, the 1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positions are substituted with one or two methyl groups. The 3-, 4- and 5-positions of the benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment F have the following structural formula ##STR26## wherein

R⁵⁰ is C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, optionally substituted with halogen, more preferably methyl and trifluoromethyl;

R⁵¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁵¹ is hydrogen or methyl;

R⁵² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl or ##STR27## wherein

R^(a) is C₁ -C₄ alkyl, more preferably R⁵² is hydrogen or methyl; or

R⁵¹ and R⁵² together are alkylene having 3 to 6 carbon atoms;

R⁵³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵³ is hydrogen or methyl;

R⁵⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵⁴ is hydrogen or methyl;

R⁵⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl; most preferably R⁵⁵ is hydrogen or methyl;

R⁵⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferably methyl, most preferably R⁵⁶ is hydrogen;

R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, with the proviso that R⁵⁷ is not attached to the 6-position.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The term "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkyl groups with one or more hydrogens replaced by chloro, bromo, iodo or fluoro.

Preferably, R⁵⁷ is in the 3-position. Most preferably R⁵⁷ is hydrogen and R⁵⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

Salts of the above-described compounds (as defined hereinafter) are also the subject of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR28## wherein R⁵⁰, R⁵¹, R⁵², R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ and R⁵⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by any base to give a salt having an anion of the following four resonance forms: ##STR29## wherein R⁵⁰, R⁵¹, R⁵², R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ and R⁵⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metal e.g. lithium, sodium, and potassium organic cations such as substituted ammonium, sulfonium or phosphonium wherein the substituent is an aliphatic or aromatic group.

Embodiment G of this invention relates to 2-benzoyl-1,3,5-cyclohexanetriones and their use as herbicides.

Embodiment G' of this invention is an herbicidal composition comprising an herbicidally active 2-benzoyl-substituted-1,3,5-cyclohexanetrione and an inert carrier therefor. The 4- and 6-positions of the 1,3,5-cyclohexanetrione moiety are preferably substituted with groups hereinafter defined, most preferably with all methyl groups. The benzoyl moiety can be substituted, preferably with the groups hereinafter recited.

The novel compounds of Embodiment G have the following structural formula ##STR30## wherein R⁶⁰ is hydrogen; halogen C₁ -C₂ alkyl, preferably methyl; C₁ -C₂ alkoxy, preferably methoxy; nitro; cyano; C₁ -C₂ haloalkyl, preferably trifluoromethyl; R^(a) SO_(n) -- wherein n is 0 or 2, preferably 2 and R^(a) is C₁ -C₂ alkyl, preferably methyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoromethoxy. Preferably, R⁶⁰ is chlorine, bromine, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, trifluoromethyl, cyano, nitro, C₁ -C₂ alkylthio or C₁ -C₂ alkylsulfonyl; more preferably chlorine, nitro, methyl, trifluoromethyl or methylsulfonyl; and

R⁶¹ is hydrogen or C₁ -C₄ alkyl, preferably methyl;

R⁶² is hydrogen or C₁ -C₄ alkyl, preferably methyl; or

R⁶¹ and R⁶² together are C₂ -C₅ alkylene;

R⁶³ is C₁ -C₄ alkyl, preferably methyl;

R⁶⁴ is C₁ -C₄ alkyl, preferably methyl; or

R⁶³ and R⁶⁴ together are C₂ -C₅ alkylene;

R⁶⁵ and R⁶⁶ independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferably chloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined; or (13) --N(R^(c))C(O)R^(d) wherein R^(c) and R^(d) are as defined.

Preferably R⁶⁵ is in the 3-position. More preferably R⁶⁵ is hydrogen, chlorine, fluorine, trifluoromethyl, cyano, C₁ -C₄ alkoxy or C₁ -C₄ thioalkyl. Most preferably, R⁶⁵ is hydrogen. Preferably R⁶⁶ is in the 4-position. Most preferably R⁶⁶ is halogen, cyano, trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl or C₁ -C₄ haloalkyl, preferably chloromethyl, difluoromethyl or trifluoromethyl.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includes chlorine, bromine, iodine and fluorine. The terms "C₁ -C₄ alkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy. The term "C₁ -C₄ haloalkyl" includes the alkyl groups defined above under C₁ -C₄ alkyl in which one or more hydrogens is replaced by chlorine, bromine, iodine or fluorine.

Salts of the above-described compounds (as defined hereinafter) are included within the scope of the instant invention.

The compounds of this invention can have the following four structural formulae because of tautomerism: ##STR31## wherein R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵ and R⁶⁶ are as defined above.

The circled proton on each of the four tautomers is reasonably labile. These protons are acidic and can be removed by reaction with a base to form a salt having an anion of the following four resonance forms: ##STR32## wherein R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵ and R⁶⁶ are as defined above.

Examples of cations of these bases are inorganic cations such as alkali metals, e.g., lithium, sodium and potassium; the alkaline earth metals, e.g. calcium and magnesium or ammonium or organic cations such as substituted ammonium, sulfonium, sulfoxonium or phosphonium wherein the substituents are aliphatic or aromatic groups.

Those skilled in the art will recognize in considering the salts of this invention that varying degrees of association between the anion and cation will exist depending upon the nature of the cation. In some instances with a suitable cation, such as copper, the salt can exist in a chelated form.

The compounds of this invention and their salts are active herbicides of a general type. That is, they are herbicidally effective against a wide range of plant species. The method of controlling undesirable vegetation of the present invention comprises applying an herbicidally effective amount of the above-described compounds to the area where control is desired.

The compounds of Embodiments A and A' of the present invention can be prepared by the following general method. ##STR33##

Generally, mole amounts of the dione and substituted benzoyl cyanide are used, along with a slight mole excess of zinc chloride. The two reactants and the zinc chloride are combined in a solvent such as methylene chloride. A slight mole excess of triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for 5 hours.

The reaction product is worked up by conventional techniques.

The above-described substituted benzoyl cyanide can be prepared according to the teaching of T. S. Oakwood and C. A. Weisgerber, Organic Synthesis Collected, Vol. III, pp. 122 (1955).

The following example teaches the synthesis of a representative compound of Embodiments A and A' of this invention.

EXAMPLE 1-A,A' 2-(2,4-Dichlorobenzoyl)-cyclohexane-1,3-dione ##STR34##

1,3-Cyclohexanedione [11.2 grams (g), 0.1 mole], 20.0 g (0.1 mole) 2,4-dichlorobenzoyl cyanide and 13.6 g (0.11 mole) anhydrous, powdered zinc chloride were combined in 100 milliliters (ml) methylene chloride. Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml 5% Na₂ CO₃ four times. The aqueous washings were combined and acidified with HCl, extracted with methylene chloride, dried and concentrated to yield 25.3 g of crude product. The crude product was dissolved in ether and stirred with 250 ml of 5% copper (II) acetate. The resulting copper salt was filtered, washed with ether and stirred with 6N hydrochloric acid to destroy the salt. The extract was washed with ether to yield 22.15 grams of the desired product m.p. 138°-140° C. (77.7% yield). The structure was confirmed by instrumental analysis.

The compounds of Embodiment B of the present invention can be prepared by the following general method. ##STR35##

Generally, mole amounts of the dione and substituted benzoyl cyanide are used, along with a slight mole excess of zinc chloride. The two reactants and the zinc chloride are combined in a solvent such as methylene chloride. A slight mole excess of triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for 5 hours.

The reaction product is worked up by conventional techniques.

The above-described substituted benzoyl cyanide can be prepared according to the teaching of T. S. Oakwood and C. A. Weisgerber, Organic Synthesis Collected, Vol. III, pp. 122 (1955).

The following example teaches the synthesis of a representative compound of Embodiment B of this invention.

EXAMPLE 1-B 4,4-Dimethyl-2-(2,4-dichlorobenzoyl)-cyclohexane-1,3-dione ##STR36##

4,4-Dimethyl-1,3-cyclohexanedione [14.0 grams (g), 0.1 mole], 20.0 g (0.1 mole) 2,4-dichlorobenzoyl cyanide and 13.6 g (0.11 mole) anhydrous, powdered zinc chloride were combined in 100 milliliters (ml) methylene chloride. Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml 5% Na₂ CO₃ four times. The aqueous washings were combined and acidified with HCl, extracted with methylene chloride, dried and concentrated to yield 25.3 g of crude product. The crude product was chromatographed (2% AcOH/CH₂ Cl₂) in 5 g aliquots then reduced on rotavap under reduced pressure at 50° C. for 30 minutes to remove AcOH. This yielded an oil (40% yield). The structure was confirmed by instrumental analysis.

The compounds of Embodiment C of the present invention can be prepared by the following general method. ##STR37##

Generally, in step (1) mole amounts of the dione and substituted benzoyl chloride are used, along with a slight mole excess of triethylamine. The two reactants are combined in a solvent such as methylene chloride. The triethylamine is slowly added to the reaction mixture with cooling. The mixture is stirred at room temperature for several hours.

The reaction product is worked up by conventional techniques. ##STR38##

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the triethylamine, preferably 2 moles of the triethylamine and up to 0.5 mole, preferably 0.1 mole of a cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot for about one hour at room temperature and the desired product is recovered by conventional techniques.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR39## wherein R²⁷ and R²⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of the The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are two representative examples of the methods described therein. ##STR40## wherein R²⁷ and R²⁸ are as previously defined.

In reaction (a) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR41## wherein R²⁷ and R²⁸ are as previously defined.

In reaction (b) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following example teaches the synthesis of a representative compound of Embodiment C of this invention.

EXAMPLE 1-C 2-(2'-Cyanobenzoyl)-4,4-dimethyl-1,3-cyclohexanedione ##STR42##

2-Cyanobenzoyl chloride (3.9 g, 24 mmol) and 4,4-dimethyl-1,3-cyclohexanedione (3.3 g, 24 mmol) were dissolved in 75 ml methylene chloride. Triethylamine (5.0 ml, 36 mmol) was added dropwise and the resulting solution stirred for one and one-half hours at room temperature. The solution was washed with water, 2 normal hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (4.4 ml, 32 mmol) and acetone cyanohydrin (5 drops) were added and the solution stirred for two hours. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified with concentrated hydrochloric acid and extracted with ether. The ether was washed with water and brine, dried (MgSO₄) and concentrated under vacuum. The residue was purified by silica gel chromatography, yielding 1.2 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiments D and D' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR43## wherein R³¹ through R³⁸ and moderate base are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl--C(O)--O--, C₁ -C₄ alkoxy--C(O)--O-- or ##STR44## wherein R³⁷ and R³⁸ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete. ##STR45## wherein the moderate base and R³¹ through R³⁸ are as defined above.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR46## wherein R³⁷ and R³⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons (1970).

The following are three representative examples of the methods described therein. ##STR47## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR48## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR49## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (c) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following examples teach the synthesis of representative compounds of Embodiment D and D' of this invention.

EXAMPLE 1-D,D' 2-(2'-Nitrobenzoyl)-1,3-cyclohexanedione ##STR50##

2-Nitrobenzoyl chloride (5.0 g, 27 mmol) and cyclohexanedione (3.0 g, 27 mmol) were dissolved in methylene chloride. Triethylamine (4.9 ml, 35 mmol) was added dropwise and the resulting solution stirred for one hour. The solution was washed with 2 normal hydrochloric acid (2N HCl), water, 5% potassium carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (1 equivalent) and potassium cyanide (40 mol %) were added and the solution stirred for one hour at room temperature. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% potassium carbonate solution. The aqueous extract was acidified and ether was added. Filtration of the resulting mixture yielded 3.2 g of the desired compound (m.p. 132°-135° C.) which was identified by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

EXAMPLE 2-D,D' 2-(2'-Nitrobenzoyl)-5,5-dimethyl-1,3-cyclohexanedione ##STR51##

Triethylamine (3.4 ml, 25 mmol) was added dropwise to a methylene chloride solution of 2-nitrobenzoyl chloride (3.5 g, 19 mmol) and 5,5-dimethylcyclohexanedione (2.4 g, 19 mmol). After stirring for one hour at room temperature an additional 3 equivalents of triethylamine and 0.4 ml acetone cyanohydrin were added. The solution was stirred for 2.5 hours, then washed with 2N HCl and extracted with 5% potassium carbonate solution. The basic extracts were acidified with 2N HCl and extracted with ether. The ether portion was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was recrystallized from ethyl acetate yielding 2.0 g of the desired compound (m.p. 130°-133° C.) which was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiments E and E' of the present invention can be prepared by the following two or three step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR52## wherein moderate base, and R⁴⁰ through R⁴⁸ are defined herein, and X is halogen, preferably chlorine, C₁ -C₄ alkyl--C(O)--O--, C₁ -C₄ alkoxy--C(O)--O-- or ##STR53## wherein R⁴⁰, R⁴⁷ and R⁴⁸ in this portion of the molecule are identical with those in the reactant shown above, and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete. ##STR54## Moderate Base=As defined herein.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetonecyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpansive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an mount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50° C. ##STR55## wherein n is 1 or 2.

Generally in step (3), a mole of the reaction product of step (2) is reacted with a slight mole or two mole excess of an oxidizing agent such as m-chloroperbenzoic acid after being dissolved in a solvent such as methylene chloride. After completion of the reaction, the resulting mixture is stripped under vacuum. The residue is purified by silica gel chromatography to yield the desired product.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR56## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are three representative examples of the methods described therein. ##STR57## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR58## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR59## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as defined and X is chlorine, bromine or iodine.

In reaction (c) the substituted aromatic halide is allowed to react with magnesium in a solvent such as ether. The solution is then poured over crushed dry ice and the benzoic acid is isolated by conventional techniques.

The following examples teach the synthesis representative compounds of Embodiments E and E' of this invention.

EXAMPLE 1-E,E' 2-(2'-Methylthiobenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR60##

2-Methylthiobenzoyl chloride (7.2 g, 39 mmol) and 4,4,6-trimethylcyclohexanedione (5.0 g, 39 mmol) were dissolved in methylene chloride. Triethylamine (7.0 ml, 50 mmol) was added dropwise and the resulting solution stirred for one hour at room temperature. The solution was washed with 2 normal hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (2.5 equivalents) and acetone cyanohydrin (0.4 ml) were added and the solution stirred for 45 minutes at room temperature. After dilution with ether, the solution was washed with 2N HCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified with hydrochloric acid and extracted with ether. The ether was washed with brine, dried (MgSO₄) and concentrated under vacuum. The residue was purified by trituration with ether, yielding 5.0 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy (nmr), infrared spectroscopy (ir) and mass spectroscopy (ms).

EXAMPLE 2-E,E' 2-(2'-Methanesulfonylbenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR61##

The benzoyl cyclohexanedione prepared in Example 1 (2.5 g, 7.9 mmol) was dissolved in 40 ml methylene chloride. m-Chloroperbenzoic acid (3.5 g, 16 mmol) was added and the resulting solution was stirred for 45 minutes. The solution was concentrated under vacuum. Purification of the residue by silica gel chromatography yielded 1.7 g of a viscous oil which was identified as the desired compound by nmr, ir and ms.

EXAMPLE 3-E,E' 2-(4'-Trifluoromethyl-2'-methanesulfinylbenzoyl)-4,4-dimethyl-1,3-cyclohexanedione ##STR62##

2-(4'-Trifluoromethyl-2'-methylthiobenzoyl)-4,4-dimethyl-1,3-cyclohexanedione (5.0 g, 14 mmol) (which was prepared according to the method of Example 1) was dissolved in 50 ml methylene chloride. A solution of m-chloroperbenzoic acid (2.4 g - 80%, 14 mmol) in 50 ml methylene chloride was added dropwise and the resulting solution was stirred for three hours at room temperature. After concentration under vacuum, the residue was dissolved in ether and washed with 1% hydrochloric acid. A 5% copper(II) acetate solution was added to the ether fraction, followed by hexane. The liquid phase was decanted and the remaining gummy solid stirred with 6N HCl and ether. The ether layer was dried (MgSO₄) and concentrated to give 4.7 of a thick yellow solid. Purification on a centrifugally accelerated thin layer chromatograph (4 mm silica gel, 50:50:1 hexane:ethyl acetate:acetic acid - eluent) yielded 2.4 g of a viscous oil which was identified as the desired compound by nmr, ir and ms.

The compounds of Embodiments F and F' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR63## wherein R⁵⁰ through R⁵⁸ are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl--C(O)--O--, C₁ -C₄ alkoxy--C(O)--O-- or ##STR64## wherein R⁵⁰, R⁵⁷ and R⁵⁸ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate and dimethylformamide. The base or benzoyl reactant preferably are added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete.

The reaction product is worked up by conventional techniques. ##STR65## Moderate base=as defined herein. wherein R⁵⁰ through R⁵⁸ are as defined.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably around 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 80° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction at about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases such as tertiary amines and inorganic bases such as alkali metal carbonates and phosphates. Suitable tertiary amines include trialkylamines such as triethylamine. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the Crown ethers.

A number of different solvents may be usable in this process, depending on the nature of the acid chloride or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR66## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are four representative examples of the methods described therein. ##STR67## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR68## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR69## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as defined and X is chlorine, bromine or iodine.

The substituted aromatic halide is allowed to react with magnesium in a solvent such as ether. The solution is then poured over crushed dry ice and the benzoic acid is isolated by conventional techniques.

The following example teaches the synthesis of a representative compound of Embodiments F and F' of this invention.

EXAMPLE 1-F,F' 2-(4'-Bromo-2'-trifluoromethylbenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR70##

4-Bromo-2-trifluoromethylbenzoyl chloride (4.3 g, 15 mmol) and 4,4,6-trimethyl-1,3-cyclohexanedione (2.3 g, 15 mmol) were dissolved in 100 ml methylene chloride. The solution was cooled with an ice bath and triethylamine (2.1 ml, 15 mmol) in 10 ml methylene chloride was added dropwise. The ice bath was then removed and the resulting solution stirred for 30 minutes at room temperature. The solution was washed with 2N hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloride solution (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue (5.1 g) was dissolved in 20 ml acetonitrile. Triethylamine (3.5 ml, 25 mmol) and 0.4 ml acetone cyanohydrin were added and the solution stirred for two hours at room temperature while protected by a drying tube (calcium sulfate). After dilution with ether, the solution was washed with 2N HCl and extracted with 5 % K₂ CO₃. The aqueous extract was acidified with concentrated hydrochloric acid and extracted with ether. The ether was washed with brine, dried (MgSO₄) and concentrated under vacuum. The resulting oil was purified on a silica gel column (80:20:1 hexane:ehtyl acetate:acetic acid - eluent), yielding 1.5 g of a viscous oil which was identified as the desired compound by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The compounds of Embodiment G and G' of the present invention can be prepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate as shown in reaction (1). The final product is obtained by rearrangement of the enol ester as shown in reaction (2). The two reactions may be conducted as separate steps by isolation and recovery of the enol ester using conventional techniques prior to conducting step (2), or by addition of a cyanide source to the reaction medium after the formation of the enol ester, or in one step by inclusion of the cyanide source at the start of reaction (1). ##STR71## wherein R⁶⁰ through R⁶⁶ and moderate base are as defined and X is halogen, preferably chlorine, C₁ -C₄ alkyl--C(O)--O--, C₁ -C₄ alkoxy--C(O)--O-- or ##STR72## wherein R⁶⁰, R⁶⁵ and R⁶⁶ in this portion of the molecule are identical with those in the reactant shown above and the moderate base is as defined, preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the trione and substituted benzoyl reactant are used, along with a mole amount or excess of the base. The two reactants are combined in an organic solvent such as methylene chloride, toluene, ethyl acetate or dimethylformamide. The base or benzoyl reactant preferably is added to the reaction mixture with cooling. The mixture is stirred at 0° C.-50° C. until the reaction is substantially complete. ##STR73## wherein the moderate base and R⁶⁰ through R⁶⁶ are as defined above.

Generally, in step (2) a mole of the enol ester intermediate is reacted with 1 to 4 moles of the moderate base, preferably about 2 moles of moderate base and from 0.01 mole to about 0.5 mole or higher, preferably about 0.1 mole of the cyanide source (e.g., potassium cyanide or acetone cyanohydrin). The mixture is stirred in a reaction pot until the rearrangement is substantially complete at a temperature below 50° C., preferably about 20° C. to about 40° C., and the desired product is recovered by conventional techniques.

The term "cyanide source" refers to a substance or substances which under the rearrangement conditions consists of or generates hydrogen cyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of a source of cyanide anion and/or hydrogen cyanide, together with a molar excess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium and potassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4 carbon atoms in the alkyl groups, such as acetone or methyl isobutyl ketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphatic aldehydes such as acetaldehye, propionaldehyde, etc., cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanide is considered most advantageous as it produces relatively rapid reaction and is inexpensive. Among cyanohydrins the preferred cyanide source is acetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percent based on the enol ester. It may be used in as little as about 1 mole percent to produce an acceptable rate of reaction about 40° C. on a small scale. Larger scale reactions give more reproducible results with slightly higher catalyst levels of about 2 mole percent. Generally about 1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enol ester, of a moderate base. By the term "moderate base" is meant a substance which acts as a base yet whose strength or activity as a base lies between that of strong bases such as hydroxides (which could cause hydrolysis of the enol ester) and that of weak bases such as bicarbonates (which would not function effectively). Moderate bases suitable for use in this embodiment include both organic bases, e.g., trialkylamines such as triethylamine and inorganic bases such as alkali metal carbonates and phosphates. Suitable inorganic bases include potassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per mole of enol ester, preferably abut 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularly potassium cyanide, a phase transfer catalyst may be included in the reaction. Particularly suitable phase transfer catalysts are the crown ethers.

A number of different solvents are useful in this process, depending on the nature of the acid halide or the acylated product. A preferred solvent for this reaction is 1,2-dichloroethane. Other solvents which may be employed, depending on the reactants or products include toluene, acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, and methyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanide source, the rearrangement may be conducted at temperatures up to about 50° C.

The above described substituted benzoyl chlorides can be prepared from the corresponding substituted benzoic acids according to the teaching of Reagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp. 767-769 (1967). ##STR74## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety of general methods according to the teaching of The Chemistry of Carboxylic Acids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y. (1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson, J. Wiley and Sons, (1970).

The following are three representative examples of the methods described therein. ##STR75## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux in aqueous sulfuric acid for several hours. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR76## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux for several hours in an aqueous hypochlorite solution. The mixture is cooled and the reaction product is isolated by conventional techniques. ##STR77## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (c) the substituted toluene is heated to reflux in an aqueous solution of potassium permanganate for several hours. The solution is then filtered and the reaction product is isolated by conventional techniques.

The following examples teaches the synthesis of a representative compound of Embodiment G and G' of this invention.

EXAMPLE 1-G,G' 2-(2'-Nitro-4'-chlorobenzoyl)-4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione ##STR78##

2-Nitro-4-chlorobenzoyl chloride (2.2 g, 10 mmol) and 4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione (1.8 g, 10 mmol) were dissolved in methylene chloride. Triethylamine was added and the resulting solution stirred at room temperature for 30 minutes. The solution was washed with 1 normal hydrochloric acid (1N HCl), and saturated sodium chloride (brine), dried over anhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine (5 ml, 3.5 equivalents) and acetone cyanohydrin (0.5 g, 0.6 equivalent) were added and the mixture stirred at room temperature for 4 hours. After dilution with ether, the solution was washed with 1N HCl and extracted with 5% K₂ CO₃. The basic extract was acidified with HCl and extracted with ether. The ether extract was washed with brine, dried over MgSO₄ and concentrated under vacuum, yielding 2.2 g of crude product. This was recrystallized from benzene to remove syncarpic acid still present. Concentration of the mother liquor under vacuum gave 1.7 g of the desired product as an oil, which solidified on standing (m.p. 76°-82° C.). It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

The following are tables of certain selected compounds of Embodiments A-G' that are preparable according to the procedures described herein. Compound numbers are assigned to each compound and are used throughout the remainder of the application.

                                      TABLE I-A                                    __________________________________________________________________________      ##STR79##                                                                     Cmpd.                                                  n.sub.D.sup.30 or       No.  R         R.sup.1                                                                            R.sup.2                                                                              R.sup.3      R.sup.4    R.sup.5                                                                              m.p.                    __________________________________________________________________________                                                            °C.              1A   CH.sub.3  CH.sub.3                                                                           Cl    H            H          H     1.5613                  2A   CH.sub.3  CH.sub.3                                                                           Cl    H            4-Cl       H     1.5655                  3A   CH.sub.3  CH.sub.3                                                                           Cl    H            H          6-Cl  103-108                 4A*  H         H   Cl    H            4-Cl       H     138-140                 5A   CH.sub.3  CH.sub.3                                                                           Br    H            H          H                             6A   CH.sub.3  CH.sub.3                                                                           Cl    H            H          5-Cl  74-77                   7A   H         H   Cl    H            H          5-Cl  104-107                 8A   H         H   Br    H            H          H     93-96                   9A   H         H   Cl    H            H          H     79-87                   10A  H         H   I     H            H          H     66-70                   11A  H         H   Cl    H            4-NO.sub. 2                                                                               H     118-122                 12A  H         H   Cl    H            H          6-Cl  143-148                 13A  H         H   Cl    H            H          5-Br  109-115                 14A  H         H   I     3-I          H          5-I   164-167                 15A  H         H   Cl    H            H          5-CH.sub.3                                                                           60-65                   16A  H         H   Cl    H            4-CH.sub.3 H     79-86                   17A  H         H   Cl    H            4-CH.sub.3 O                                                                              H     60-63                   18A  H         H   Cl    3-Cl         H          6-Cl                          19A  H         H   Cl    H            H          5-CH.sub.3 O                                                                         77-80                   20A  H         H   Cl    3-Cl         H          H     80-90                   21A  H         H   Cl    H            H          5-CF.sub.3                                                                           74-75                   22A  H         H   Cl    H            H          5-NO.sub.2                                                                           140-143                 23A  H         H   Cl    3-Cl         4-Cl       H     152-154                 24A  H         H   Cl    3-Cl         4-CH.sub.3 O                                                                              H     169-170                 25A  H         H   Cl    H            4-Br       H     104-107                 26A  CH.sub.3  CH.sub.3                                                                           CH.sub.3 O                                                                           H            H          H     104-108                 27A  H         H   Cl    H                                                                                            ##STR80## H                             28A  H         H   Br    H            H          (a)                           29A  H         H   CH.sub.3 O                                                                           3-CH.sub.3 O H          H     75-79                   30A  H         H   CH.sub.3 O                                                                           H            H          5-CH.sub.3 O                                                                         89-92                   31A  H         H   Br    H            4-CH.sub.3 O                                                                              5-CH.sub.3 O                                                                         92-96                   32A H         H  Br    H           (4)-OCH.sub.2 O-(5)                                                                            63-68                       33A CH.sub.3  CH.sub.3                                                                          Cl    3-Cl        4-Cl      H     86-89                       34A H         H  Cl    3-Cl        H         5-Cl                              35A CH.sub.3  CH.sub.3                                                                          Cl    3-Cl        H         5-Cl  105-109                     36A CH.sub.3  CH.sub.3                                                                          Cl    3-Cl        4-Cl      5-Cl  137-139                     37A H         H  Cl    3-Cl        4-Cl      5-Cl  106-110                     38A H         H  Cl    H           4-Cl      5-Cl  108-111                     39A                                                                                 ##STR81##                                                                               H  Cl    H           4-Cl      H                                 40A                                                                                 ##STR82##                                                                               H  Cl    H           4-Cl      H                                 41A CH(CH.sub.3).sub.2                                                                       H  Cl    H           4-Cl      H                                 42A CH(CH.sub.3).sub.2                                                                       H  Cl    3-Cl        4-Cl      H                                 43A H         H  Cl    H           4-F       H                                 44A sodium salt of Compound No. 23                 85-94                       45A isopropylamine salt of Compound No. 23         160-165                     46A triethylamine salt of Compound No. 23          82-85                       47A potassium salt of Compound No. 23              107-106                     48A triethanolammonium salt of Compound No. 39                                 49A sodium salt of Compound No. 43                 60-63                       50A CH(CH.sub.3).sub.2                                                                       H  Cl    3-CH.sub.3 O                                                                               4-Br      H                                 51A H         H  Cl    H           4-CH.sub.3 SO.sub.2                                                                      H     140-141                     52A H         CH.sub.3                                                                          Cl    H           4-Cl      H                                 53A i-C.sub.4 H.sub.9                                                                        H  Cl    H           4-Cl      H                                 54A i-C.sub.3 H.sub.7                                                                        H  Cl    3-CH.sub.3 O                                                                               H         H                                 55A CH.sub.3  CH.sub.3                                                                          Cl    H           4-CH.sub.3 SO.sub.2                                                                      H                                 56A CH.sub.3  CH.sub.3                                                                          Cl    3-CH.sub.3  4-Cl      H                                 57A H         H  Cl    3-CH.sub.3  4-Cl      H     56-64                       58A H         H  Cl    H           4-C.sub.2 H.sub.5 SO.sub.2                                                               H     98-102                      59A H         H  Cl    3-Cl        4-C.sub.2 H.sub.5 SO.sub.2                                                               H     98-109                      60A H         H  Cl    H           4-C.sub.3 H.sub.7 SO.sub.2                                                               H     semi-solid                  61A H         H  Cl    3-CH.sub.3 O                                                                               4-CH.sub.3 SO.sub.2                                                                      H     48-59                       62A CH.sub.3  CH.sub.3                                                                          Cl    H           4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H     semi-solid                  63A H         H  Cl    3-Cl        4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H     145-148.5                   64A H         H  Cl    3-C.sub.2 H.sub.5 S                                                                        4-C.sub.2 H.sub.5 SO.sub.2                                                               H     oil                         65A CH.sub.3  CH.sub.3                                                                          Cl    H           4-C.sub.2 H.sub.5 SO.sub.2                                                               H     103-108                     66A CH.sub.3  CH.sub.3                                                                          Cl    3-Cl        4-C.sub.2 H.sub.5 SO.sub.2                                                               H     108-114                     67A i-C.sub.3 H.sub.7                                                                        H  Cl    H           4-C.sub.2 H.sub.5 SO.sub.2                                                               H     brown gum                   68A H         H  Cl    3-Cl        4-CH.sub.3 SO.sub.2                                                                      H     145-154                     69A i-C.sub.3 H.sub.7                                                                        H  Cl    3-Cl        4-CH.sub.3 SO.sub.2                                                                      H                                 70A H         H  Br    H           4-CH.sub.3 SO.sub.2                                                                      H     brown gum                   71A H         H  Cl    H           4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H     semi-solid                  72A H         H  Cl    H           4-CH.sub.3 S                                                                             H     74-77                       73A H         H  Cl    3-Cl        4-CH.sub.3 S                                                                             H                                 74A CH.sub.3  CH.sub.3                                                                          Cl    3-Cl        4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H     120-123                     75A H         H  Cl    H           4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H     semi-solid                  76A CH.sub.3  CH.sub.3                                                                          Cl    H           4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H                                 77A H         H  Cl    3-C.sub.2 H.sub.5 O                                                                        4-CH.sub.3 SO.sub.2                                                                      H     semi-solid                  78A H         H  Cl    3-CH.sub.3 O                                                                               4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H     golden gum                  79A CH.sub.3  CH.sub.3                                                                          Cl    H           4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H     125-128                     80A CH(CH.sub.3).sub.2                                                                       H  CH.sub.3 O                                                                           3-Cl        5-Cl      H                                 81A H         H  Cl    3-CH.sub.3 O                                                                               4-Br      H     101-111                     82A H         H  Cl    3-CH.sub.3  4-Cl      H     56-64                       83A H         H  Cl    H           4-Cl      5-CH.sub.3 O                                                                         softens >70                 84A CH(CH.sub.3).sub.2                                                                       H  Cl    3-n-C.sub.3 H.sub.7 O                                                                      4-Br      H                                 85A H         H  Cl    3-C.sub.2 H.sub.5 O                                                                        4-Br      H     101-104                     86A H         H  Cl    H           4-i-C.sub.4 H.sub.9 SO.sub.2                                                             H     136-140                     87A CH.sub.3  CH.sub.3                                                                          Cl    H           4-i-C.sub.4 H.sub.9 SO.sub.2                                                             H                                 88A H         H  Cl    3-Cl        4-i-C.sub.3 H.sub.7 SO.sub.2                                                             H     173-176                     89A H         H  Cl    3-Cl        4-n-C.sub.4 H.sub.9 SO.sub.2                                                             H     135-138                     90A H         H  Cl    3-C.sub.2 H.sub.5 O                                                                        4-C.sub.2 H.sub.5 SO.sub.2                                                               H     gum                         91A H         H  Cl    3-CH.sub.3 O                                                                               4-C.sub.2 H.sub.5 SO.sub.2                                                               H     gum                         92A H         H  Cl    3-Cl        4-C.sub.2 H.sub.5 S                                                                      H     91-94                       93A H         H  Cl    3-C.sub.2 H.sub.5 S                                                                        4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H     oil                         94A H         H  Cl    3-C.sub.2 H.sub.5 S                                                                        4-C.sub.2 H.sub.5 S                                                                      H     oil                         95A H         H  Cl    H           4-(CH.sub.3).sub.2 NSO.sub.2                                                             H     oil                         96A H         H  Cl    3-C.sub.2 H.sub.5 O                                                                        4-n-C.sub.3 H.sub.7 SO.sub.2                                                             H                                 97A H         H  Cl    3-n-C.sub.3 H.sub.7 O                                                                      4-C.sub.2 H.sub.5 SO.sub.2                                                               H     oil                         98A CH.sub.3  CH.sub.3                                                                          Cl    H           4-(CH.sub.3).sub.2 NSO.sub.2                                                             H     oil                         99A H         H  Cl    H           4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                      H     90-92                       100A                                                                               CH.sub.3  CH.sub.3                                                                          Cl    H           4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                      H                                 101A                                                                               H         H  Cl    H           4-C.sub.2 H.sub.5 S                                                                      H                                 102A                                                                               H         H  Cl    H           4-n-C.sub.3 H.sub.7 S                                                                    H                                 103A                                                                               H         H  Cl    H           4-i-C.sub.3 H.sub.7 S                                                                    H                                 104A                                                                               H         H  Cl    H           4-C.sub.2 H.sub.5 SO                                                                     H                                 105A                                                                               H         H  CH.sub.3 O                                                                           H           4-NO.sub.2                                                                               H     semi-solid                  106A                                                                               H         H  Cl    3-n-C.sub.3 H.sub.7 O                                                                      4-Br      H                                 107A                                                                               H         H  Cl    3-n-C.sub.3 H.sub.7 O                                                                      4-CH.sub.3 SO.sub.2                                                                      H     96-100                      108A                                                                               H         H  Cl    3-allyloxy  4-CH.sub.3 SO.sub.2                                                                      H     semi-solid                  109A                                                                               H         H  Cl    3-CH.sub.3 C(O)NH                                                                          4-Cl      H     155-160                     110A                                                                               H         H  Cl    3-Cl        4-n-C.sub.3 H.sub.7 S                                                                    H                                 111A                                                                               H         H  Cl    3-CH.sub.3 O                                                                               4-NO.sub.2                                                                               H     150-153                     112A                                                                               H         H  Cl    3-allyloxy  4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                 113A                                                                               H         H  Cl    3-CH.sub.2 BrCHBrCHBrCH.sub.2 O                                                            4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                 114A                                                                               H         H  Cl    3-n-C.sub.4 H.sub.9 O                                                                      4-C.sub.2 H.sub.5 SO.sub.2                                                               H     gum                         115A                                                                               H         H  Cl    3-i-C.sub.4 H.sub.9 O                                                                      4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                 116A                                                                               H         H  Cl    H           4-allylthio                                                                              H                                 117A                                                                               CH.sub.3  CH.sub.3                                                                          Cl    H           4-NO.sub.2                                                                               H                                 118A                                                                               H         H  Cl    3-CH.sub.3 C(O)N(CH.sub.3)                                                                 4-Cl      H                                 119A                                                                               H         H  Cl    3-i-C.sub.3 H.sub.7 O                                                                      4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                 120A                                                                               H         H  Cl    3-CH.sub.2 ClCH.sub.2 CH.sub.2 O                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                               H     gum                         121A                                                                               H         H  Cl    H           4-t-C.sub.4 H.sub. 9 S                                                                   H                                 122A                                                                               H         H  Cl    3-CH.sub.3 O                                                                               4-C.sub.2 H.sub.5 S                                                                      H                                 123A                                                                               H         H  Cl    H           4-CF.sub.3                                                                               H                                 124A                                                                               H         H  Cl    H           4-Cl      6-Cl                              125A                                                                               H         H  Cl    3-CH.sub.3 C(O)N(CH.sub.3)                                                                 H         H     131-135                     126A                                                                               H         H  Cl    3-CH.sub.3 C(O)NH                                                                          H         H                                 127A                                                                               H         H  Cl    3-(CH.sub.3).sub.2 N                                                                       4-Cl      H                                 128A                                                                               CH.sub.3  H  Cl    3-CH.sub.3 O                                                                               4-CH.sub.3 SO.sub.2                                                                      H     117-122                     129A                                                                               H         H  Cl    H           4-C.sub.2 H.sub.5 SO.sub.2                                                               H                                 130A                                                                               H         H  Br    H           H         H                                 131A                                                                               H         H  Br    H           4-C.sub.2 H.sub.5 OC(O)                                                                  H                                 132A                                                                               H         H  Cl    H           4-CN      H     183-184                     133A                                                                               H         H  Cl    3-CH.sub.3 C(O)NH                                                                          H         6-NO.sub.2                        134A                                                                               H         H  Cl    3-(CH.sub.3).sub.2 N                                                                       H         H                                 135A                                                                               H         H  Cl    3-Cl        4-ClCH.sub.2 CH.sub.2 SO.sub.2                                                           H                                 __________________________________________________________________________      *Prepared in Example 1A.                                                       ##STR83##                                                                

                                      TABLE I-B                                    __________________________________________________________________________      ##STR84##                                                                     Com-                                                                           pound                                                                          Number                                                                              R.sup.10 R.sup.11                                                                           R.sup.12                                                                           R.sup.13                                                                              R.sup.14   R.sup.15                                                                          R.sup.16                                                                          R.sup.17                                                                          R.sup.18                      __________________________________________________________________________     1B                                                                                   ##STR85##                                                                              H   Cl  H      4-Cl       H  H  H  H                             2B                                                                                   ##STR86##                                                                              CH.sub.3                                                                           Cl  H      4-Cl       H  H  H  H                             3B   triethanolammonium salt of Compound No. 2                                 4B   triethanolammonium salt of Compound No. 7                                 5B                                                                                   ##STR87##                                                                              CH.sub.3                                                                           Cl  3-Cl   4-Cl       H  H  H  H                             6B   triethanolammonium salt of Compound No. 5                                 7B.sup.a                                                                            CH.sub.3 CH.sub.3                                                                           Cl  H      4-Cl       H  H  H  H                             8B   CH.sub.3 CH.sub.3                                                                           Cl  H      4-Cl       CH.sub.3                                                                          H  H  H                             9B   CH.sub.3 n-C.sub.3 H.sub.7                                                                  Cl  H      4-Cl       H  H  H  H                             10B  CH.sub.3 H   Cl  H      4-Cl       H  H  H  H                             11B  CH.sub.3 H   Cl  H      4-Cl       CH.sub.3                                                                          H  H  H                             12B  C.sub.5 H.sub.10                                                                            Cl  H      4-Cl       H  H  H  H                             13B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-Cl       H  H  H  H                             14B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-Cl       CH.sub.3                                                                          H  H  H                             15B  i-C.sub.3 H.sub.7                                                                       H   Cl  3-Cl   4-Cl       H  H  H  H                             16B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-CH.sub.3 SO.sub.2                                                                       H  H  H  H                             17B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-CH.sub.3 SO.sub.2                                                                       CH.sub.3                                                                          H  H  H                             18B  CH.sub.3 H   Cl  H      4-CH.sub.3 SO.sub.2                                                                       H  H  H  H                             19B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-CH.sub.3 SO.sub.2                                                                       H  H  H  H                             20B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             21B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             22B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-C.sub.2 H.sub.5 SO.sub.2                                                                CH.sub.3                                                                          H  H  H                             23B  CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             24B  CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                       H  H  H  H                             25B  CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3                                                                            4-Cl       H  H  H  H                             26B  CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                           4-Cl       H  H  H  H                             27B  CH.sub.3 C.sub.2 H.sub.5                                                                    Cl  H      4-Cl       H  H  H  H                             28B  CH.sub.3 CH.sub.3                                                                           Cl  H      H          H  H  H  H                             29B  CH.sub.3 CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                           4-Br       H  H  H  H                             30B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-Br       H  H  H  H                             31B  CH.sub.3 C.sub.2 H.sub.5                                                                    Cl  3-Cl   4-Cl       H  H  H  H                             32B  n-C.sub.3 H.sub.7                                                                       H   Cl  H      4-Cl       H  H  H  H                             33B                                                                                  ##STR88##                                                                              n-C.sub.3 H.sub.7                                                                  Cl  H      4-Cl       H  H  H  H                             34B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-i-C.sub.3 H.sub.7 SO.sub.2                                                              H  H  H  H                             35B  CH.sub.3 CH.sub.3                                                                           Cl  3-i-C.sub.3 H.sub.7 O                                                                 4-Br       H  H  H  H                             36B  CH.sub.3 CH.sub.3                                                                           Cl  H      6-F        H  H  H  H                             37B  i-C.sub.3 H.sub.7                                                                       H   Cl  3-Cl   4-Cl       H  H  H  H                             38B  CH.sub.3 CH.sub.3                                                                           Cl  3-OC.sub.2 H.sub.5                                                                    4-Br       CH.sub.3                                                                          H  H  H                             39B  i-C.sub.3 H.sub.7 OC(O)                                                                 H   Cl  H      4-Cl       H  H  H  H                             40B  C.sub.2 H.sub.5 OC(O)                                                                   n-C.sub.3 H.sub.7                                                                  Cl  H      4-Cl       H  H  H  H                             41B  C.sub.5 H.sub.10                                                                            Cl  H      4-Cl       H  H  H  H                             42B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-Cl       H  H  CH.sub.3                                                                          H                             43B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-n-C.sub.3 H.sub.7 SO.sub.2                                                              H  H  H  H                             44B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-n-C.sub.3 H.sub.7 SO.sub.2                                                              H  H  H  H                             45B  CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         3-CH.sub.3 O                                                                          H          H  H  H  H                             46B  CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H      4-Cl       H  H  H  H                             47B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-Br       CH.sub.3                                                                          H  H  H                             48B  CH.sub.3 CH.sub.3                                                                           Br  H      H          H  H  H  H                             49B  CH.sub.3 CH.sub.3                                                                           I   H      H          H  H  H  H                             50B  CH.sub.3 CH.sub.3                                                                           F   H      H          H  H  H  H                             51B  CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H      H          H  H  H  H                             52B  CH.sub.3 CH.sub.3                                                                           Cl  3-allyloxy                                                                            4-Br       H  H  H  H                             53B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-CH.sub.3 SO.sub.2                                                                       H  H  CH.sub.3                                                                          H                             54B  CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                          4-Br       CH.sub.3                                                                          H  H  H                             55B  CH.sub.3 CH.sub.3                                                                           Br  H      4-CN       H  H  H  H                             56B  CH.sub.3 CH.sub. 3                                                                          Cl  H      4N(CH.sub.3)SO.sub.2 CF.sub.3                                                             H  H  H  H                             57B  CH.sub.3 CH.sub.3                                                                           Cl  3-NO.sub.2                                                                            H          H  H  H  H                             58B  CH.sub.3 CH.sub.3                                                                           C.sub.2 H.sub.5 O                                                                  H      4-Cl       H  H  H  H                             59B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-i-C.sub.4 H.sub.9 SO.sub.2                                                              H  H  H  H                             60B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                   4-CH.sub.3 SO.sub.2                                                                       H  H  H  H                             61B  CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             62B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-n-C.sub.4 H.sub.9 SO.sub.2                                                              H  H  H  H                             63B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-n-C.sub.4 H.sub.9 SO.sub.2                                                              CH.sub.3                                                                          H  H  H                             64B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                                CH.sub.3                                                                          H  H  H                             65B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-F        H  H  H  H                             66B  CH.sub.3 H   Cl  3-CH.sub.3 O                                                                          4-Br       H  H  H  H                             67B  CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                          H          H  H  H  H                             68B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                   4-n-C.sub.3 H.sub.7 SO.sub.2                                                              H  H  H  H                             69B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                   4-C.sub.2 H.sub.5 S                                                                       H  H  H  H                             70B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                   4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             71B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 S                                                                   4-CH.sub.3 SO.sub.2                                                                       H  H  H  H                             72B  CH.sub.3 CH.sub.3                                                                           Cl  Cl     4-i-C.sub.3 H.sub.7 SO.sub.2                                                              H  H  H  H                             73B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-n-C.sub.4 H.sub.9 SO.sub.2                                                              H  H  H  H                             74B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                   4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             75B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                   4-Br       H  H  H  H                             76B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                   4-n-C.sub.3 H.sub.7 SO.sub.2                                                              H  H  H  H                             77B  CH.sub.3 CH.sub.3                                                                           Cl  3-n-C.sub.3 H.sub.7 O                                                                 4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             78B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-(CH.sub.3).sub.2 NSO.sub.2                                                              H  H  H  H                             79B  CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 S                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             80B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-C.sub.2 H.sub.5 S                                                                       H  H  H  H                             81B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-C.sub.2 H.sub.5 S                                                                       H  H  H  H                             82B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                       H  H  H  H                             83B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-n-C.sub.3 H.sub.7 SO.sub.2                                                              H  H  H  H                             84B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-n-C.sub.3 H.sub.7 S                                                                     CH.sub.3                                                                          H  H  H                             85B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-C.sub.2 H.sub.5 S(O)                                                                    H  H  H  H                             86B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-i-C.sub.3 H.sub.7 S                                                                     H  H  H  H                             87B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-n-C.sub.3 H.sub.7 S                                                                     H  H  H  H                             88B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-t-C.sub.4 H.sub.9 SO.sub.2                                                              H  H  H  H                             89B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-i-C.sub.3 H.sub.7 S                                                                     CH.sub.3                                                                          H  H  H                             90B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-n-C.sub.3 H.sub.7 SO.sub.2                                                              CH.sub. 3                                                                         H  H  H                             91B  CH.sub.3 CH.sub.3                                                                           Cl  *      4-Cl       H  H  H  H                             92B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-CH.sub.2CHCH.sub.2 S                                                                    H  H  H  H                             93B  CH.sub.3 CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                   4-C.sub.2 H.sub.5 S                                                                       H  H  H  H                             94B  CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-CH.sub.3 S                                                                              CH.sub.3                                                                          H  H  H                             95B  CH.sub.3 CH.sub.3                                                                           Cl  H      4-CH.sub.3 S                                                                              H  H  H  H                             96B  CH.sub.3 CH.sub.3                                                                           Cl  3-i-C.sub.3 H.sub.7 O                                                                 4-C.sub.2 H.sub.5 SO.sub.2                                                                H  H  H  H                             97B  CH.sub.3 CH.sub.3                                                                           Cl  3-CH.sub.3 O                                                                          4-C.sub.2 H.sub.5 S                                                                       H  H  H  H                             98B  CH.sub.3 CH.sub.3                                                                           Cl  **     4-Cl       H  H  H  H                             99B  CH.sub.3 CH.sub.3                                                                           Cl  **     H          H  H  H  H                             100B CH.sub.3 CH.sub.3                                                                           Cl  3-Cl   4-CH.sub.3 S                                                                              H  H  H  H                             101B CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H      4-NO.sub.2 H  H  H  H                             102B CH.sub.3 CH.sub.3                                                                           CH.sub.3 O                                                                         H      4-CF.sub.3 H  H  H  H                             103B CH.sub.3 CH.sub.3                                                                           Cl  H      4-n-C.sub.3 H.sub.7 SO                                                                    H  H  H  H                             104B CH.sub.3 CH.sub.3                                                                           Cl  H      4-n-C.sub.3 H.sub.7 SO                                                                    CH.sub.3                                                                          H  H  H                             __________________________________________________________________________      .sup.a Prepared in Example IB.                                                 *β-CH.sub.3 C(O)NH                                                        **3-CH.sub.3 C(O)N(CH.sub.3)                                             

The following additional compounds can be prepared by the general method hereinbefore taught.

                                      TABLE I-B                                    __________________________________________________________________________      ##STR89##                                                                     R.sup.10                                                                           R.sup.11                                                                           R.sup.12                                                                           R.sup.13                                                                             R.sup.14                                                                             R.sup.15                                                                           R.sup.16                                                                          R.sup.17                                                                          R.sup.18                                     __________________________________________________________________________     CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  H     4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  H     4-Cl  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  H     4-Cl  CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  H     4-Cl  H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  H     4-Cl  CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  H     4-Cl  H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  H     4-Cl  CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  H     4-Cl  H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  H     4-Cl  CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  H     4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-Cl  4-Cl  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-Cl  4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-Cl  4-Cl  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-Cl  4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-Cl  4-Cl  H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-Cl  4-Cl  CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-Cl  4-Cl  H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-Cl  4-Cl  CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-Cl  4-Cl  H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-Cl  4-Cl  CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-Cl  4-Cl  H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-Cl  4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  H     4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  H     4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  H     4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  H     4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  H     4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  H     4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  H     4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  H     4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  H     4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  H     4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  H     4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  H     4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  H     4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           H   Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub. 3                                                                          n-C.sub.4 H.sub.9                                                                  Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-CH.sub.3                                                                           4-C.sub. 2 H.sub.5 SO.sub.2                                                          CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                      H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-CH.sub.3                                                                           4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-CH.sub.3                                                                           4-Cl  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-CH.sub.3                                                                           4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-CH.sub.3                                                                           4-Cl  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-CH.sub.3                                                                           4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-CH.sub.3                                                                           4-Cl  H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-CH.sub.3                                                                           4-Cl  CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-CH.sub.3                                                                           4-Cl  H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-CH.sub.3                                                                           4-Cl  CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-CH.sub.3                                                                           4-Cl  H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-CH.sub.3                                                                           4-Cl  CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-CH.sub.3                                                                           4-Cl  H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-CH.sub.3                                                                           4-Cl  CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-CH.sub.3                                                                           4-Cl  H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-CH.sub.3                                                                           4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-OCH.sub.3                                                                          4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-OCH.sub.3                                                                          4-Cl  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl  3-OCH.sub.3                                                                          4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-OCH.sub.3                                                                          4-Cl  H   H  H  H                                            CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl  3-OCH.sub.3                                                                          4-Cl  CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           H   Cl  3-OCH.sub.3                                                                          4-Cl  H   H  H  H                                            CH.sub.3                                                                           H   Cl  3-OCH.sub.3                                                                          4-Cl  CH.sub.3                                                                           H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-OCH.sub.3                                                                          4-Cl  H   H  H  H                                            C.sub.2 H.sub.5                                                                    H   Cl  3-OCH.sub.3                                                                          4-Cl  CH.sub.3                                                                           H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-OCH.sub.3                                                                          4-Cl  H   H  H  H                                            n-C.sub.4 H.sub.9                                                                  H   Cl  3-OCH.sub.3                                                                          4-Cl  CH.sub.3                                                                           H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-OCH.sub.3                                                                          4-Cl  H   H  H  H                                            i-C.sub.3 H.sub.7                                                                  H   Cl  3-OCH.sub.3                                                                          4-Cl  CH.sub.3                                                                           H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-OCH.sub.3                                                                          4-Cl  H   H  H  H                                            C.sub.5 H.sub.10                                                                       Cl  3-OCH.sub.3                                                                          4-Cl  CH.sub.3                                                                           H  H  H                                             CH.sub.3                                                                          CH.sub.3                                                                           Cl  3-n-C.sub.3 H.sub.7 O                                                                4-Br  H   H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                           H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  H     4-NO.sub.2                                                                           H   H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-C.sub.2 H.sub.5 O                                                                  4-CH.sub.3 S                                                                         H   H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  H     4-CN  H   H  H  H                                            CH.sub.3                                                                           CH.sub.3                                                                           Cl  3-(CH.sub.3).sub.2 N                                                                 4-Cl  H   H  H  H                                            __________________________________________________________________________

                                      TABLE I-C                                    __________________________________________________________________________      ##STR90##                                                                     Comp. No.                                                                            R.sup.21                                                                          R.sup.22                                                                          R.sup.23                                                                          R.sup.24                                                                          R.sup.25                                                                          R.sup.26                                                                          R.sup.27                                                                          R.sup.28                                                                          n.sub.D.sup.30 or m.p.                           __________________________________________________________________________      1C.sup.a                                                                            CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H  H  oil                                              2C    H  H  H  H  H  H  H  CN 124-140° C.                               __________________________________________________________________________      .sup.a Prepared in Example IC.                                           

                                      TABLE I-D                                    __________________________________________________________________________      ##STR91##                                                                     Comp.                                                                          No. R.sup.31                                                                          R.sup.32                                                                           R.sup.33                                                                           R.sup.34                                                                          R.sup.35                                                                          R.sup.36                                                                          R.sup.37                                                                            R.sup.38 n.sub.D.sup.30 or                        __________________________________________________________________________                                           m.p.                                      1D CH.sub.3                                                                          H   H   H  H  H  H    H        viscous oil                               2D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    H        viscous oil                               3D.sup.a                                                                          H  H   H   H  H  H  H    H        132-135                                   4D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    H        viscous oil                               5D.sup.b                                                                          H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    H        130-133                                   6D CH.sub.3                                                                          H   H   H  CH.sub.3                                                                          H  H    H        viscous oil                               7D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    CF.sub.3 52-61                                     8D H  H   H   H  H  H  H    CF.sub.3 88-94                                     9D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    CF.sub.3 89-97                                    10D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3                                                                          H        119-122                                  11D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-Cl H        72-79                                    12D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    Cl       118-121                                  13D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-Cl H        118-120                                  14D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-F  H        130-133                                  15D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3 O                                                                        H        139-142                                  16D CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                                                           H  H  H  H    CF.sub.3 viscous oil                              17D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    NO.sub.2 viscous oil                              18D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    Br       viscous oil                              19D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  CH.sub.3                                                                          5-CH.sub.3                                                                          H        viscous oil                              20D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-CH.sub.3                                                                          H        viscous oil                              21D H  H   H   H  H  H  H    F        123-128                                  22D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    F        viscous oil                              23D H  H   H   H  H  H  H    Cl       viscous oil                              24D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CH.sub.3                                                                       130-133                                  25D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 -n-C.sub.3 H.sub.7                                                             viscous oil                              26D H  H   H   H  H  H  H    SO.sub.2 CH.sub.3                                                                       157-159                                  27D H  H   H   H  H  H  H    SO.sub.2 -n-C.sub.3 H.sub.7                                                             120-123                                  28D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-F  H        165-195                                  29D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2C.sub.2 H.sub.5                                                                 oil                                      30D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    SO.sub.2CH.sub.3                                                                        gum                                      31D CH.sub.3                                                                          n-C.sub.4 H.sub.9                                                                  H   H  H  H  H    H        viscous oil                              32D H  H   i-C.sub.4 H.sub.9                                                                  H  H  H  H    H        viscous oil                              33D H  H   H   H  H  H  H    SO.sub.2C.sub.2 H.sub.5                                                                 viscous oil                              34D H  H   H   H  H  H  H    CN       viscous oil                              35D H  H   H   H  H  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                              158-159                                  36D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                              120-130                                  37D H  H   H   H  H  H  H    SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       158-163                                  38D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       oil                                      39D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H                                                                                    ##STR92##                                                                              oil                                      40D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    SO.sub.2N(C.sub.2 H.sub.5).sub.2                                                        oil                                      41D H  H   H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      42D H  H   H   H  H  H  H    S(O)-n-C.sub.3 H.sub.7                                                                  oil                                      43D H  H   H   H  H  H  H    S-n-C.sub.3 H.sub.7                                                                     oil                                      44D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    S-n-C.sub.3 H.sub.7                                                                     oil                                      45D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    S-n-C.sub.3 H.sub.7                                                                     oil                                      46D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    SC.sub.2 H.sub.5                                                                        oil                                      47D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      47D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SC.sub.2 H.sub.5                                                                        oil                                      48D H  H   H   H  H  H  H    SCH.sub.3                                                                               94-97                                    49D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    CF.sub.3 oil                                      50D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SCH.sub.3                                                                               oil                                      51D .sup.c                                                                            H   i-C.sub.3 H.sub.7                                                                  H  H  H  H    H        145-148                                  52D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  5-CH.sub.3 O                                                                        Br       oil                                      53D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    Cl       oil                                      54D H  H   H   H  H  H  3-CH.sub.3 O                                                                        Cl       oil                                      55D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  3-CH.sub.3 O                                                                        Cl       oil                                      56D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    CH.sub.3 S                                                                              oil                                      57D H  H   H   H  H  H  H                                                                                    ##STR93##                                                                              120-125                                  58D H  H   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H    CN       175-177                                  59D CH.sub. 3                                                                         CH.sub.3                                                                           H   H  H  H  H    CN       151-153                                  60D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  H    CN       oil                                      61D .sup.c                                                                            H   H   H  H  H  H    H        oil                                      62D .sup.d                                                                            H   H   H  H  H  H    H        oil                                      63D H  H   CH.sub.3                                                                           H  H  H  H    Cl       110-115                                  64D H  H   CH.sub.3                                                                           H  H  H  H    SO.sub.2 -n-C.sub.3 H.sub.7                                                             oil                                      65D .sup.d                                                                            CH.sub.3                                                                           H   H  H  H  H    Cl       oil                                      66D H  H   H   H  H  H  H    SO.sub.2 CHCl.sub.2                                                                     oil                                      67D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CHCl.sub.2                                                                     oil                                      68D H  H   H   H  H  H  .sup.c                                                                              Br       oil                                      69D H  H   H   H  H  H  H    SO.sub.2 CH.sub.2 Cl                                                                    oil                                      70D CH.sub.3                                                                          CH.sub.3                                                                           H   H  H  H  H    SO.sub.2 CH.sub.2 Cl                                                                    wax                                      71D .sup.d                                                                            CH.sub.3                                                                           H   H  H  H  H    H        oil                                      72D H  H   H   H  H  H  C.sub.2 H.sub.5 O                                                                   Cl       oil                                      73D CH.sub.3                                                                          CH.sub.3                                                                           H   H  CH.sub.3                                                                          H  CH.sub.3 O                                                                          CF.sub.3 oil                                      __________________________________________________________________________      .sup. a Prepared in Example ID,D'.                                             .sup.b Prepared in Example 2D,D'.                                              .sup.c = C.sub.2 H.sub.5 OC(O)-                                                .sup.d = iC.sub.3 H.sub.7 OC(O)-                                         

                                      TABLE I-E                                    __________________________________________________________________________      ##STR94##                                                                     Comp.                                                                          No. n R.sup.40                                                                           R.sup.41                                                                          R.sup.42                                                                          R.sup.43                                                                          R.sup.44                                                                          R.sup.45                                                                          R.sup.46                                                                          R.sup.47                                                                           R.sup.48                                                                              m.p.                                    __________________________________________________________________________     1E  0 CH.sub.3                                                                           H  H  H  H  H  H  H   H      79-81° C.                        2E  0 CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                     3E.sup.a                                                                           0 CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                          H  H   H      oil                                     4E.sup.b                                                                           2 CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                          H  H   H      oil                                     5E  0 C.sub.2 H.sub.5                                                                    CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                     6E  2 C.sub.2 H.sub.5                                                                    CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   H      oil                                     7E  0 CH.sub.3                                                                           H  H  H  H  H  H  3-Cl                                                                               Cl     59-64° C.                        8E  2 CH.sub.3                                                                           H  H  H  H  H  H  3-Cl                                                                               Cl     116-119° C.                      9E  0 CH.sub.3                                                                           H  H  H  H  H  H  H   CF.sub.3                                                                              102-106° C.                      10E 2 CH.sub.3                                                                           H  H  H  H  H  H  H   CF.sub.3                                                                              oil                                     11E 0 CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                              49-53° C.                        12E 2 CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                              oil                                     13E.sup.c                                                                          1 CH.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H   CF.sub.3                                                                              oil                                     14E 0 CH.sub.3                                                                           H  H  H  H  H  H  3-Cl                                                                               SCH.sub.3                                                                             105-107° C.                      15E 1 CH.sub.3                                                                           H  H  H  H  H  H  3-Cl                                                                               S(O)CH.sub.3                                                                          oil                                     16E 0 CH.sub.3                                                                           H  H  H  H  H  H  H   SO.sub.2 n-C.sub.3 H.sub.7                                                            oil                                     17E 0 CH.sub.3                                                                           H  H  H  H  H  H  H   SCH.sub.3                                                                             101-103° C.                      18E 2 CH.sub.3                                                                           H  H  H  H  H  H  H   SO.sub.2 n-C.sub.3 H.sub.7                                                            oil                                     19E 2 CH.sub.3                                                                           H  H  H  H  H  H  H   SO.sub.2 CH.sub.3                                                                     194-196° C.                      20E 0 CH.sub.3                                                                           H  H  H  H  H  H  3-CH.sub.3                                                                         H      40-42° C.                        21E 2 CH.sub.3                                                                           H  H  H  H  H  H  3-CH.sub.3                                                                         H      80-86° C.                        __________________________________________________________________________      .sup.a Prepared in Example 1E,E'.                                              .sup.b Prepared in Example 2E,E'.                                              .sup.c Prepared in Example 3E,E'.                                        

                                      TABLE I-F                                    __________________________________________________________________________      ##STR95##                                                                     Comp.                                          n.sub.D.sup.30                  No. R.sup.50                                                                           R.sup.51                                                                           R.sup.52                                                                           R.sup.53                                                                            R.sup.54                                                                           R.sup.55                                                                           R.sup.56                                                                           R.sup.57                                                                            R.sup.58 or m.p.                         __________________________________________________________________________     1F  CH.sub.3                                                                           H   H   H    H   H   H   H    H        35-42° C.                2F  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    H        47-53° C.                3F  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    Br       oil                             4F  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    CN       oil                             5F  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   3-NO.sub.2                                                                          H        oil                             6F  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   5-Cl H        oil                             7F  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    CH.sub.3 SO.sub.2                                                                       oil                             8F  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   CH.sub.3                                                                           H   H    CH.sub.3 SO.sub.2                                                                       oil                             9F  CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   3-Cl H        oil                             10F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   CH.sub.3                                                                           H   H    C.sub.2 H.sub.5 SO.sub.2                                                                oil                             11F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    C.sub.2 H.sub.5 SO.sub.2                                                                oil                             12F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    n-C.sub.3 H.sub.7 SO.sub.2                                                              oil                             13F CH.sub.3                                                                           H   H   H    H   H   H   H    CH.sub.3 SO.sub.2                                                                       oil                             14F CH.sub.3                                                                           H   H   H    H   H   H   H    n-C.sub.3 H.sub.7 SO.sub.2                                                              oil                             15F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    CH.sub.3 S                                                                              oil                             16F C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    Br       oil                             17F CH.sub.3                                                                           H   H   H    H   H   H   H    CN       oil                             18F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    F        oil                             19F CH.sub.3                                                                           H   H   H    H   H   H   H    C.sub.2 H.sub.5SO.sub.2                                                                 oil                             20F CH.sub.3                                                                           H   H   H    H   H   H   3-Cl H        65-67° C.                21F CH.sub.3                                                                           H   H   H    H   H   H   3-I  H        oil                             22F CH.sub.3                                                                           H   H   H    H   H   H   3-NO.sub.2                                                                          H        oil                             23F CH.sub.3                                                                           H   H   H    H   H   H   3-CN H        96-101° C.               24F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    H        oil                             25F CF.sub.3                                                                           H   H   H    H   H   H   H    H        oil                             26F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    Br       oil                             27F CF.sub.3                                                                           H   H   H    H   H   H   H    Cl       82-88° C.                28F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    Cl       oil                             29F CF.sub.3                                                                           H   H   H    H   H   H   H    C.sub.2 H.sub.5 S                                                                       oil                             30F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    C.sub.2 H.sub.5 SO.sub.2                                                                oil                             31F CF.sub.3                                                                           H   H   H    H   H   H   H    CN       oil                             32F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    CN       oil                             33F.sup.a                                                                          CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   CH.sub.3                                                                           H   H    Br       oil                             34F CH.sub.3                                                                           H   H   H    H   H   H   H    CH.sub.3                                 35F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   3-Cl C.sub.2 H.sub.5 SO.sub.2                                                                115-117° C.              36F CH.sub.3                                                                           H   H   H    H   H   H   3-Cl C.sub.2 H.sub.5 SO.sub.2                                                                oil                             37F CH.sub.3                                                                           .sup.b                                                                             .sup.b                                                                             H    H   H   H   3-CF.sub.3                                                                          H        oil                             38F CH.sub.3                                                                           .sup.c                                                                             H   i-C.sub.3 H.sub.7                                                                   H   H   H   3-NO.sub.2                                                                          H        88-108° C.               39F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   CH.sub.3                                                                           H   H    CH.sub.3 S                                                                              oil                             40F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    CH.sub.3 S                                                                              oil                             41F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   CH.sub.3                                                                           H   H    CH.sub.3 SO.sub.2                                                                       oil                             42F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    CF.sub.3 oil                             43F CH.sub.3                                                                           H   H   H    H   H   H   H    CF.sub.3 114-120° C.              44F CH.sub.3                                                                           H   H   H    H   H   H   3-Cl Cl       oil                             45F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   3-Cl Cl       oil                             46F CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   3-CF.sub.3                                                                          H        oil                             47F CF.sub.3                                                                           H   H   H    H   H   H   H    CH.sub.3 S                                                                              oil                             48F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   CH.sub.3                                                                           H   H    CF.sub.3 oil                             49F CF.sub.3                                                                           H   H   H    H   H   H   H    CF.sub.3 oil                             50F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   H   H   H    CF.sub.3 oil                             51F CH.sub.3                                                                           H   H   CH.sub.3                                                                            H   H   H   H    CH.sub.3 SO.sub.2                                                                       oil                             52F CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    H   CH.sub.3                                                                           H   H    C.sub.2 H.sub.5 SO.sub.2                                                                oil                             53F CH.sub.3                                                                           H   H   H    H   H   H   H    Br       94-98° C.                54F CH.sub.3                                                                           H   H   H    H   H   H   .sup.d                                                                              H        oil                             __________________________________________________________________________      .sup.a Prepared in Example 1F,F'.                                              .sup.b (CH.sub.2).sub.5                                                        .sup.c C.sub.2 H.sub.5 OC(O)-                                                  .sup. d 3-N(CH.sub.3)COCH.sub.3                                          

                                      TABLE I-G                                    __________________________________________________________________________      ##STR96##                                                                     Comp.                                                                          No.  R.sup.60                                                                             R.sup.61                                                                          R.sup.62                                                                          R.sup.63                                                                          R.sup.64                                                                          R.sup.65                                                                            R.sup.66                                                                               m.p. °C.                            __________________________________________________________________________     1G   NO.sub.2                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    H       112-117                                    2G.sup.a                                                                            NO.sub.2                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    76-82                                      3G   Cl    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.3                                                                    176-179°                            4G   CH.sub.3                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                        5G   CF.sub.3                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             viscous oil                                6G   NO.sub.2                                                                             CH.sub. 3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.2 Cl                                                                 oil                                        7G   Cl    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-F     gum                                        8G   Cl    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-OC.sub.2 H.sub.5                                                                  4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                        9G   NO.sub.2                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 CH.sub.3                                                                    gum                                        10G  Cl    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCH.sub.3                                                                            gum                                        11G  CH.sub.3                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-NO.sub.2                                                                          H       gum                                        12G  I     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    H       gum                                        13G  OCH.sub.3                                                                            CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    gum                                        14G  Cl    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-OCH.sub.3                                                                         4-Br    gum                                        15G  NO.sub.2                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 nC.sub.3 H.sub.7                                                            gum                                        16G  NO.sub.2                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2 N(CH.sub.3).sub.2                                                           gum                                        17G  NO.sub.2                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CN    148-150°                            18G  SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub. 3                                                                         H    H       gum                                        19G  NO.sub.2                                                                             CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             gum                                        20G  H     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-Cl    gum                                        21G  H     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCF.sub.3                                                                            gum                                        22G  H     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-OCF.sub.3                                                                            gum                                        23G  Cl    CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          3-Cl 4-SO.sub.2 C.sub.2 H.sub.5                                                             gum                                        24G  H     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-C(O)CH.sub.3                                                                         gum                                        25G  H     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SO.sub.2CH.sub.3                                                                     129-131                                    26G  H     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-SCH.sub.3                                                                            89-92                                      27G  H     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CF.sub.3                                                                             115-125                                    28G  H     CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H    4-CN    87-95                                      __________________________________________________________________________      .sup.a prepared in Example 1G,G'.                                        

HERBICIDAL SCREENING TESTS

As previously mentioned, the herein described compounds produced in the above-described manner are phytotoxic compounds which are useful and valuable in controlling various plant species. Selected compounds of this invention were tested as herbicides in the following manner.

Pre-emergence herbicide test. On the day preceding treatment, seeds of eight different weed species are planted in loamy sand soild in individual rows using one species per row across the width of a flat. The seeds used are green foxtail (FT) (Sertaria viridis), watergrass (WG) (Echinochloa crusgalli), wild oat (WO) (Avena fatua), annual morningglory (AG) (Ipomoea lacunosa), velvetleaf (VL) (Abuilon theophrasti), Indian mustard (MD) (Brassica juncea), redroot pigweed (PW) (Amaranthus retroflexus) or curly dock (CD) (Rumex crispus) and yellow nutsedge (YNG) (Cyperus esculentus). Ample seeds are planted to give about 20 to 40 seedlings per row, after emergence, depending upon the size of the plants.

Using an analytical balance, 600 milligrams (mg) of the compound to be tested are weighed out on a piece of glassine weighing paper. The paper and compound are placed in a 60 milliliter (ml) wide-mouth clear bottle and dissolved in 45 ml of acetone or substituted solvent. Eighteen ml of this solution are transferred to a 60 ml wide-mouth clear bottle and diluted with 22 ml of a water and acetone mixture (19:1) containing enough polyoxyethylene sorbitan monolaurate emulsifier to give a final solution of 0.5% (v/v). The solution is then sprayed on a seeded flat on a linear spray table calibrated to deliver 80 gallons per acre (748 L/ha). The application rate is 4 lb/ acre (4.48 kg/ha).

After treatment, the flats are placed in the greenhouse at a temperature of 70° to 80° F. and watered by sprinkling. Two weeks after treatment, the degree of injury or control is determined by comparison with untreated check plants of the same age. The injury rating from 0 to 100% is recorded for each species as percent control with 0% representing no injury and 100% representing complete control.

The results of the tests are shown in the following Tables

                                      TABLE II-A                                   __________________________________________________________________________     Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No. FT  WG  WO  AMG VL  MD  PW  CD  YNS                                        __________________________________________________________________________      1A 100 90  20  40  65  50  35      80                                          2A 80  90  0   30  80  90  20      90                                          3A 0   0   0   40  40  40  0       0                                           4A 100 100 50  35  100 100 90      95                                          5A 100 95  65  35  90  85  50      95                                          6A 50  25  0   25  100 100 35      80                                          7A 80  90  10  60  100 100 100     80                                          8A 95  95  45  40  100 80  95      95                                          9A 95  100 55  30  100 90  100     95                                         10A 100 100 60  20  85  100 100     95                                         11A 85  100 30  40  100 100 100     95                                         12A 85  85  90  75  80  95  90      90                                         13A 85  75  10  10  85  65  95      90                                         14A 40  10  80  0   65  40  65      100                                        15A 40  60  20  30  100 30  75      95                                         16A 80  80  20  55  75  90  40      95                                         17A 20  --  10  25  100 95  85      90                                         18A 65  --  30  70  100 100 85      90                                         19A 45  60  0   30  40  0   20      60                                         20A 30  85  20  40  95  85  40      45                                         21A 80  100 0   80  100 100 95      95                                         22A 20  10  0   20  75  30  45      10                                         23A 45  95  10  0   100 85  100     95                                         24A --  100 0   25  70  90  --      100                                        25A --  100 25  80  100 100 --      100                                        26A 40  15  0   0   0   10      0   30                                         27A 40  80  10  20  60  50      30  75                                         28A 65  75  0   65  100 95      75  55                                         29A 100 95  55  10  80  75      85  95                                         30A 20  20  20  10  40  40      50  20                                         31A 75  95  20  20  100 95      75  10                                         32A 90  85  20  0   100 85      75  30                                         33A 80  70  0   40  20  40      90  80                                         34A 60  40  0   20  95  100     100 60                                         35A 0   10  0   0   10  20      20  10                                         36A 0   0   0   20  100 100     100 0                                          37A 40  0   0   20  100 60      90  --                                         38A 10  40  0   20  90  80      20  20                                         39A 80  10  0   0   0   0       0   90                                         40A 60  0   0   0   0   0       0   90                                         41A 100 100 85  40  95  100     100 100                                        42A 60  100 25  0   0   0       0   25                                         43A 100 100 45  40  80  90      90  100                                        44A 90  100 0   60  100 100     100 95                                         45A 100 100 0   60  100 100     100 100                                        46A 20  60  0   100 100 100     100 20                                         47A 60  70  20  100 100 100     100 60                                         48A 60  0   0   0   0   0       0   40                                         49A 100 100 50  10  60  20      90  100                                        50A 100 100 80  10  60  60      90  100                                        51A 100 100 90  100 100 100     85  100                                        52A 100 100 60  10  100 100     60  100                                        53A 0   20  0   0   20  20      0   10                                         54A 10  45  10  0   0   0       0   40                                         55A 90  100 60  100 100 100     90  100                                        56A 40  70  40  40  40  60      70  50                                         57A 100 100 90  100 100 100     85  100                                        58A 90  95  0   20  20  40      40  100                                        59A 95  100 85  75  100 100     90  98                                         60A 95  100 50  50  100 100     90  98                                         61A 100 100 75  100 100 100     95  95                                         62A 100 100 95  75  100 100     100 80                                         63A 100 100 40  65  100 100     100 95                                         64A 100 100 98  100 100 100     100 90                                         65A 100 100 80  100 100 100     100 90                                         66A 100 100 75  100 100 100     100 98                                         73A 100 100 60  80  100 100     75  90                                         74A 100 100 70  80  100 100     80  100                                        75A 70  100 0   50  100 100     100 80                                         76A 40  90  25  10  100 100     100 10                                         77A 100 100 90  100 100 100     85  --                                         78A 100 100 80  100 100 100     90  --                                         79A 50  100 50  50  95  100     100 60                                         80A 0   0   0   0   0   0       0   0                                          81A 100 100 50  15  100 100     90  100                                        84A 100 100 85  0   0   100     20  100                                        88A 60  95  35  95  100 100     95  80                                         89A 75  100 40  100 100 100     95  60                                         90A 100 100 90  100 100 100     100 85                                         105A                                                                               80  95  25  0   95  50      70  50                                         117A                                                                               95  100 0   25  100 100     50  95                                         118A                                                                               100 100 60  100 100 100     100 85                                         121A                                                                               95  100 50  75  100 95      100 80                                         125A                                                                               100 100 50  80  100 100     100 85                                         126A                                                                               70  100 80  80  100 100     100 80                                         127A                                                                               100 100 100 100 100 100     --  80                                         128A                                                                               100 100 100 100 100 100     --  80                                         129A                                                                               100 100 95  90  100 100     --  80                                         131A                                                                               70  85  0   20  95  98      95  90                                         132A                                                                               100 100 95  90  100 100     --  80                                         133A                                                                               100 100 100 100 100 100     --  80                                         135A                                                                               100 100 100 80  100 100     --  80                                         __________________________________________________________________________

                                      TABLE II-B                                   __________________________________________________________________________     Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No. FT   WG  WO  AMG  VL  MD  CD   YNS                                         __________________________________________________________________________      1B 0    85  10  75   100 80  80   75                                           2B 90   100 65  100  100 100 100  100                                          4B 100  100 80  60   100 80  90   100                                          5B 80   100 20  40   100 100 80   100                                          6B 40   100 0   40   100 100 80   100                                          7B 100  100 100 80   100 100 90   100                                          8B 100  100 60  45   60  60  80   100                                          9B 60   100 40  20   60  60  60   100                                         10B 100  100 40  5    80  60  80   100                                         11B 100  100 90  10   20  20  40   100                                         12B 0    20  0   0    10  20  10   0                                           13B 100  100 90  40   100 100 100  100                                         15B 90   90  50  20   --  100 100  80                                          16B 100  100 95  100  100 100 90   100                                         17B 100  100 100 100  100 100 100  97                                          18B 100  100 85  100  100 100 90   95                                          19B 100  100 95  100  100 100 100  95                                          20B 100  100 85  100  100 100 100  90                                          21B 100  100 100 100  100 100 100  95                                          22B 100  100 80  100  100 100 100  90                                          25B 100  100 75  80   100 100 100  90                                          26B 100  100 65  30   100 100 100  90                                          27B 20   95  60  5    100 100 90   100                                         28B 100  100 80  20   90  40  80   100                                         29B 100  100 70  20   100 100 100  100                                         30B 100  100 80  60   100 100 80   100                                         31B 80   100 40  10   60  60  80   100                                         32B 20   40  10  0    --  60  100  60                                          33B 0    10  0   0    10  10  0    0                                           34B 100  100 90  80   100 100 90   100                                         35B 100  100 90  40   90  90  90   90                                          36B 100  100 85  0    95  85  95   90                                          37B 90   90  50  20   --  100 100  80                                          39B 15   100 0   50   100 80  70   40                                          40B 0    10  0   0    10  10  0    0                                           41B 0    20  0   0    10  20  10   0                                           42B 100  100 90  45   100 100 65   100                                         43B 100  100 90  100  100 100 100  90                                          44B 100  100 85  100  100 100 100  95                                          45B 65   100 0   0    100 20  20   90                                          46B 100  100 0   20   100 100 98   85                                          47B 100  100 90  85   100 100 100  95                                          48B 100  100 85  15   100 100 85   95                                          49B 100  100 65  0    100 100 50   50                                          50B 80   80  55  0    98  55  80   65                                          51B 95   95  10  0    65  0   25   60                                          52B 100  100 100 100  100 100 50                                               53B 100  100 75  100  100 100 100  50                                          54B 100  100 60  15   100 100 100  80                                          55B 100  100 55  15   100 100 90   95                                          56B 100  100 60  20   95  100 90   10                                          57B 5    10  0   0    40  20  0    0                                           58B 10   40  10  10   95  40  100  80                                          59B 100  100 75  80   100 100 100  75                                          60B 100  100 90  100  100 100 85   --                                          61B 100  100 80  100  100 100 100  --                                          62B 95   100 50  95   100 100 85   --                                          63B 100  100 70  100  90  100 100  --                                          64B 100  100 75  100  100 100 85   --                                          65B 100  100 55  40   100 100 90   70                                          66B 100  100 65  35   100 100 100  95                                          67B 100  100 30  15   100 100 95   90                                          71B 100  100 80  100  100 100 80   --                                          72B 100  100 40  100  100 100 90   75                                          73B 90   100 40  100  100 100 95   50                                          74B 100  100 85  95   100 100 90   80                                          75B 100  100 100 70   100 100 100  95                                          77B 100  100 55  40   100 100 90   70                                          81B 90   95  60  10   25  75  90   0                                           82B 40   90  20  35   100 --  75   20                                          91B 100  100 85  100  100 100 80   90                                          101B                                                                               85   90  0   0    95  50  50   75                                          __________________________________________________________________________

                  TABLE II-C                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO   AMG   VL   MD   CD   YNS                             ______________________________________                                         1C    65     80      65   55    90   90   35   0                               ______________________________________                                    

                                      TABLE II-D                                   __________________________________________________________________________     Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No. FT  WG   WO  AMG  VL  MD   CD  YNS                                         __________________________________________________________________________      1D 100 100  85  30   100 100  90  90                                           2D 100 100  100 50   100 100  95  95                                           3D 100 100  85  25   100 100  100 95                                           4D 100 100  100 20   100 85   95  90                                           5D 100 100  45  25   100 100  90  90                                           6D 100 100  95  40   100 100  85  90                                           9D 100 100  90  90   100 100  80  90                                          10D 100 90   20  10   100 70   100 90                                          11D 90  100  50  230  100 100  90  90                                          12D 100 100  95  80   100 100  90  90                                          13D 40  75   0   10   80  100  100 90                                          14D 50  0    0   0    100 80   70  90                                          15D 65  95   20  15   100 80   90  85                                          17D 100 100  60  30   100 100  90  35                                          18D 100 100  100 100  100 100  100 95                                          19D 100 100  0   50   100 100  100 95                                          20D 75  100  0   25   100 90   65  90                                          21D 100 100  100 80   100 100  90  95                                          22D 100 100  100 80   100 100  95  95                                          23D 100 100  98  95   100 100  100 95                                          25D 100 100  80  100  100 100  80  --                                          26D 100 100  75  100  100 100  80  --                                          27D 90  100  50  100  100 100  100 90                                          28D 75  50   50  0    100 100  90  65                                          30D 100 100  85  100  100 100  95  90                                          31D 85  75   0   25   100 25   0   35                                          32D 83  85   35  20   95  100  75  50                                          36D 100 100  50  100  100 100  100 75                                          37D 20  75   0   20   100 95   100 75                                          38D 85  95   40  60   100 100  75  85                                          39D 85  95   45  75   100 95   70  90                                          51D 60  60   35  0    25  0    0   30                                          52D 75  75   0   50   90  75   40  0                                           65D 100 100  80  100  100 100  --  80                                          __________________________________________________________________________      A blank (--) indicates that the weed was not tested.                     

                  TABLE II-E                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG     WO    AMG   VL   MD   CD   YNS                             ______________________________________                                         1E     0      0      0     0     0    0    0   20                              2E     25     30    30     0     70   0   40   30                              3E     25     20     0     0     0    0    0    0                              4E    100    100    90    60    100  100  100  90                              5E     50     60    40    50     50  60   90   50                              6E    100     95    50    40     40  60   99   70                              16E    80    100    50    60    100  90   90   90                              20E   100    100    30    15    100  100  90   85                              21E   100    100    --    30    100  95   100  80                              ______________________________________                                          A blank (--) indicates that the weed was not tested.                     

                                      TABLE II-F                                   __________________________________________________________________________     Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.  FT  WG  WO  AMG  VL  MD  CD  YNS                                          __________________________________________________________________________      1F  40  20  0   0    0   0   0   100                                           2F  60  70  0   0    0   0   90  100                                           3F  100 100 50  50   100 100 85  90                                            4F  100 100 90  30   100 85  95  95                                            5F  100 100 80  10   100 100 100 95                                            6F  20  35  25  15   90  85  40  85                                            7F  100 100 90  100  100 100 100 95                                            8F  100 100 90  100  100 100 100 95                                            9F  100 100 0   0    100 80  100 90                                           10F  100 100 100 100  100 100 100 95                                           11F  100 100 70  100  100 100 97  95                                           12F  100 100 60  100  100 100 100 95                                           13F  100 100 60  100  100 100 100 95                                           14F  80  100 50  80   100 100 90  90                                           15F  100 100 80  100  100 100 100  --                                          16F  50  75  0   25   100 100 95  60                                           17F  100 100 40  100  100 100 100 85                                           18F  100 100 0   20   100 100 80  70                                           20F  70  75  0   25   100 95  100 60                                           21F  50  60  0   0    100 80  80  60                                           22F  100 95  35  25   100 100 90  50                                           23F  95  100 40  20   100 100 90  50                                           24F  100 100 90  0    45  85  80  90                                           25F  100 100 25  60   100 100 100 75                                           34F  35  40  10  0    60  25  0   70                                           37F  50  60  0   0    60  0   50  0                                            38F  35  40  0   0    0   0   0   0                                            52F  85  100 30  95   100 100 --  80                                           53F  100 100 0   85   100 100 --  80                                           54F  100 100 90  25   100 100 --  80                                           __________________________________________________________________________      A blank (--) indicates that the weed was not tested.                     

                  TABLE II-G                                                       ______________________________________                                         Pre-Emergence Herbicidal Activity                                              Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT      WG      WO    AMG   VL    MD    YNS                              ______________________________________                                          1G   100     100     90    100   100   100   80                                2G   100     100     90    100   100   100   80                                3G   100     100     90    100   100   100   80                                4G   100     100     90    100   100   100   80                                5G   100     100     90    100   100   100   80                                6G*  100     100     100   100   100   --    20                                7G   100     100     80    100   100   100   80                                8G    85     100     80    100   100   100   80                                9G   100     100     80    100   100   100   80                               10G   100     100     80    100   100   100   80                               11G   100     100     80    100   100   100   80                               12G   100     100     80     90   100   100    0                               13G   100     100     70    100   100   100    0                               14G   100     100     75    100   100   100   90                               15G   100     100     80    100   100   100   90                               16G   100     100     90    100   100   100   80                               17G   100     100     80    100   100   100   80                               18G   100     100     90     85   100   100   80                               19G   100     100     100   100   100   100   80                               20G    70      95     10    100   100   100    0                               21G   100     100     100   100   100   100   80                               22G   100     100     90    100   100   100   80                               23G   100     100     100   100   100   100   80                               24G    0       80      0     25    80    70    0                               25G   100     100     80    100   100   100   80                               26G   100     100     100    80   100   100   80                               27G   100     100     100   100   100   100   80                               28G   100     100     90    100   100   100   80                               ______________________________________                                          A blank (--) indicates that the weed was not tested.                           *Tested Tested at 0.56 kg/ha.                                            

Post-Emergence Herbicide Test: This test is conducted in an identical manner to the testing procedure for the pre-emergence herbicide test, except the seeds of the eight different wed species are planted 10-12 days before treatment. Also, watering of the treated flats is confined to the soil surface and not to the foliage of the sprouted plants.

The results of the post-emergence herbicide test are reported in Table III.

                                      TABLE III-A                                  __________________________________________________________________________     Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No. FT  WG  WO  AMG VL  MD  PW  CD  YNS                                        __________________________________________________________________________      1A 60  70  20  40  60  60  35      60                                          2A 30  70  0   50  90  85  30      80                                          3A 0   30  0   70  100 90  55      70                                          4A 95  98  20  98  100 100 30      95                                          5A 80  80  75  50  60  80  0       95                                          6A 40  40  10  60  100 100 75      65                                          7A 60  75  40  60  100 75  100     75                                          8A 85  80  75  70  95  80  90      90                                          9A 85  80  75  70  95  80  90      90                                         10A 95  85  90  60  95  95  80      95                                         11A 50  80  35  55  100 100 95      80                                         12A 45  75  50  55  75  60  50      80                                         13A 30  60  20  60  80  50  60      70                                         14A 20  10  20  50  45  40  40      0                                          15A 65  95  0   65  95  30  100     80                                         16A 65  80  20  85  85  30  30      80                                         17A 75  80  30  70  100 100 85      90                                         18A 100 95  10  100 100 100 100     90                                         19A 60  80  40  70  100 75  80      90                                         20A 65  80  10  85  95  95  100     70                                         21A 30  55  0   80  100 80  65      80                                         22A 0   30  0   20  45  0   30      20                                         23A 85  90  40  85  100 95  100     90                                         24A 0   80  0   70  90  74  --      100                                        25A 100 100 75  90  100 100 --      100                                        26A 45  30  0   40  70  65      0   45                                         27A 75  80  30  65  50  45      85  85                                         28A 75  60  60  75  100 70      80  25                                         29A 85  85  85  75  85  65      65  85                                         30A 75  50  20  10  0   0       20  40                                         31A 60  60  20  40  40  70      100 40                                         32A 60  25  20  40  90  65      20  40                                         33A 10  0   0   10  10  10      100 40                                         34A 10  10  0   5   50  30      80  0                                          35A 0   0   0   10  60  30      40  0                                          36A 0   0   0   20  20  20      0   0                                          37A 0   0   0   30  40  20      80  0                                          38A 10  10  10  20  10  20      20  10                                         39A 40  40  20  0   0   0       5   80                                         40A 90  70  40  20  60  80      20  65                                         41A 60  85  85  20  40  60      100 100                                        42A 60  50  40  70  20  40      60  60                                         43A 100 80  30  60  100 100     80  100                                        44A 80  85  0   60  90  90      100 80                                         45A 90  90  10  100 100 100     100 90                                         46A 80  100 0   60  100 100     100 100                                        47A 100 100 0   60  100 100     100 100                                        48A 40  40  20  10  10  10      90  40                                         49A 40  40  40  80  100 100     60  60                                         50A 80  60  60  50  50  60      80  70                                         51A 80  80  80  95  100 100     100 90                                         52A 60  60  20  20  40  40      90  60                                         53A 10  20  20  0   0   0       0   20                                         54A 20  40  20  5   0   0       0   40                                         55A 40  40  40  60  60  60      80  90                                         56A 100 100 75  80  100 100     100 90                                         57A 80  80  80  95  100 100     100 90                                         58A 60  70  10  70  10  10      20  80                                         59A 100 100 90  100 --  100     100 50                                         60A 100 100 100 100 --  100     100 70                                         61A 90  85  90  85  --  100     100 80                                         62A 100 85  100 75  100 100     100 35                                         63A 70  80  20  100 100 100     35  40                                         64A 75  75  90  70  90  70      40  40                                         65A 100 70  100 55  90  95      100 40                                         66A 100 75  100 90  95  95      100 20                                         73A 100 100 95  100 100 100     55  30                                         74A 100 95  75  100 100 100     85  40                                         75A 100 100 30  95  80  100     80  40                                         76A 80  80  75  75  100 95      95  25                                         77A 80  80  80  90  90  80      90  80                                         78A 80  85  75  85  80  95      100 50                                         79A 50  65  35  90  100 100     90  --                                         80A 40  40  10  20  60  0       0   30                                         81A 90  70  60  40  60  60      90  70                                         84A 100 100 100 20  40  40      80  60                                         88A 100 95  90  100 85  100     100 50                                         89A 100 100 75  85  75  85      95  50                                         90A 100 85  90  90  85  90      100 55                                         91A 100 100 100 100 95  100     95  60                                         105A                                                                               35  50  --  35  100 80      60  30                                         117A                                                                               40  60  0   25  50  50      80  --                                         118A                                                                               95  85  85  100 100 90      80  80                                         121A                                                                               65  85  40  100 100 100     60  50                                         125A                                                                               90  95  75  70  100 90      100 60                                         126A                                                                               40  50  20  40  60  50      100 80                                         127A                                                                               100 95  100 95  100 100         80                                         128A                                                                               85  95  80  60  100 95          80                                         129A                                                                               65  90  60  60  100 98          70                                         130A                                                                               100 95  95  95  100 100         70                                         131A                                                                               0   20  0   0   30  75      10  0                                          132A                                                                               95  100 100 80  95  95          50                                         133A                                                                               80  95  90  60  85  85          60                                         135A                                                                               70  100 100 75  100 95          70                                         __________________________________________________________________________

                  TABLE III-B                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG     WO   AMG   VL   MD    CD   YNS                             ______________________________________                                          1 B  85     95     20   95    100  100   95   95                               2 B  90     90     80   100   90   90    --   80                               4 B  60     60     90   40    60   60    90   70                               5 B  40     60     10   20    40   40    90   80                               6 B  40     50     10   60    20   20    60   50                               7 B  80     80     80   60    60   90     6   60                               8 B  100    80     60   30    80   80    80   80                               9 B  70     70     60   40    60   60    80   70                              10 B  40     40     60   30    60   60    90   60                              11 B  80     90     60   45    90   90    100  80                              12 B  25     45     10   20    20   20    60   45                              13 B  100    100    95   70    60   60    80   60                              15 B  100    60     50   80    90   90    40   60                              16 B  60     60     80   80    90   90    60   65                              17 B  100    70     90   100   --   90    98   70                              18 B  100    85     100  85    --   100   100  65                              19 B  100    80     85   100   100  90    100  70                              20 B  90     65     90   85    70   60    100  40                              21 B  40     40     10    0     0    0     0    0                              22 B  40     70     80   90    90   100   95   40                              25 B  40     70     40   40    40   60    70   50                              26 B  65     70     80   40    90   80    70   80                              27 B  100    80     60   20    90   90    80   45                              28 B  90     60     60   60    60   60    40   70                              29 B  90     70     70   40    70   70    60   60                              30 B  100    90     70   50    100  100   80   80                              31 B  40     50     20   10    20   20     0   40                              32 B  25     40     40   90    100  100   40   40                              33 B  20     40     10   60    90   90    60   40                              34 B  90     80     80   80    100  100   80   50                              35 B  60     50     50   20    60   60    80   60                              36 B  100    80     80   75    --   100   100  45                              37 B  100    60     50   80    90   90    40   60                              39 B  90     80     25   30    30   45    50   30                              40 B  20     40     10   60    90   90    60   40                              41 B  25     45     10   20    20   20    60   45                              42 B  90     80     80   80    100  100   100  70                              43 B  80     90     95   97    100  100   100  50                              44 B  100    95     95   95    40   100   100  30                              45 B  30     65      0   30    45   40    65   50                              46 B  70     75      0   65    100  100   50   70                              47 B  100    100    100  90    100  100   100  85                              48 B  100    65     80   50    100  100   60   60                              49 B  60     70     70   40    80   70    30   50                              50 B   0     60     40   60    100  90    20   30                              51 B  100    75     80   40    100  50    20   30                              52 B  90     100    100  100   100  100   100  40                              53 B  60     70     70   70    90   65    40   60                              54 B  100    100    85   100   100  100   100  60                              55 B  95     85     90   100   100  100   90   45                              56 B  85     100     0   10    15   95    40   50                              57 B  85     70     65    0     0    0     0   35                              58 B  20     40     10   15    70   40    35   40                              59 B  100    95     100  95    100  95    100  40                              60 B  65     75     75   80    90   85    80   60                              61 B  80     80     70   95    80   85    80   50                              62 B  100    80     25   80    75   80    85   35                              63 B  100    100    40   95    95   100   95   50                              64 B  75     70     50   90    90   100   90   50                              65 B  100    80     80   60    85   60     0   --                              66 B  98     90     60   35    --   100   60   90                              67 B  70     65     20   15    95   40    70   45                              71 B  95     50     50   80    80   80    65   50                              72 B  100    85     75   75    65   85    70   60                              73 B  100    95     95   85    75   85    95   40                              74 B  100    85     95   90    80   95    65   50                              75 B  100    80     80   30    50   60    100  40                              81 B  50     80     35   70    70   90    80   10                              82 B  25     60     50   35    50   90    50   25                              91 B  80     60     40   60    75   90    60   75                              101 B 10     35     --   30    75   70    40   50                              ______________________________________                                          -- = Specie did not germinate for some reason.                           

                  TABIE III-C                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG     WO   AMG   VL   MD    CD   YNS                             ______________________________________                                         1 C   98     95     70   60    100  55    100  90                              ______________________________________                                    

                  TABLE III-D                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG     WO   AMG   VL   MD    CD   YNS                             ______________________________________                                          1 D  95     75     85   70    100  90    85   40                               2 D  45     70     95   75    100  90    100  65                               3 D  100    80     100  90    --   100   100  80                               4 D  100    80     100  100   --   100   85   75                               5 D  90     70     45   60     95  70    60   80                               6 D  95     75     80   70    100  90    90   65                               9 D  100    90     90   100   100  100   95   85                              10 D  45     75     10   15    100  100   20   75                              11 D  100    70     60   75    100  100   100  45                              12 D  100    75     100  100   100  100   90   90                              13 D  30     55       0  30     60  60    15   60                              14 D  20     65      0   40     70  60    40   25                              15 D  20     75     30   20    100  70    60   40                              17 D  85     80     50   65     95  95    100  60                              18 D  100    95     100  100   100  100   100  75                              19 D  20     95     30   100   100  35    30   70                              20 D  30     80     15   100   100  45    20   70                              21 D  100    80     100  55    100  90    100  80                              22 D  100    80     100  60    100  95    95   95                              23 D  100    90     90   100   100  100   85   70                              25 D  70     75     50   85     90  85    60   75                              26 D  100    85     85   95     95  95    90   60                              27 D  90     90     60   100   100  100   100  --                              28 D  15     45     20   50     75  80    15   30                              30 D  100    100    80   85     85  85    100  --                              31 D  80     90     100  100   100  100   100  60                              32 D  75     85     85   75     75  90    95   50                              36 D  35     50     35   70     50  50    35   60                              37 D  60     75     15   70     70  90    90   40                              38 D  95     90     65   70     90  90    100  50                              39 D  95     85     30   50     70  80    100  50                              51 D  60     75     60   35     30  60    40   60                              52 D  60     75     25   100   100  100   100  75                              65 D  70     50     70   90     80  85    --   80                              ______________________________________                                          A blank -- indicates the weed was not tested.                            

                  TA8LE III-E                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG     WO   AMG   VL   MD    CD   YNG                             ______________________________________                                         1 E   20     20     10   20    40   40    20   40                              2 E    0     60     60   50    70   30     0   15                              3 E   20     20      0   10     0   20     0   20                              4 E   85     90     100  45    75   30    80   65                              5 E   55     50     60   50    75   85    65   --                              6 E   70     70     50   60    80   70    90   --                              16 E  95     95     40   100   100  100   100  90                              20 E  95     75     35   40    95   75    35   80                              21 E  80     70     30   45    80   90    50   70                              ______________________________________                                          A blank -- indicates the weed was not tested.                            

                  TA8LE III-F                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG     WO   AMG   VL   MD    CD   YNG                             ______________________________________                                          1 F  60     40     20   30    40   40    50   60                               2 F  50     40     10   20    20   20    40   60                               3 F  100    100    85   100   100  100   100  75                               4 F  100    100    95   85    100  95    100  60                               5 F  95     95     100  65    90   25    70   45                               6 F  40     30      0   20    90   25    20   70                               7 F  100    100    100  100   100  100   100  90                               8 F  100    95     100  100   100  100   100  70                               9 F  65     65      0   20    80   65    90   80                              10 F  100    100    100  100   100  100   100  70                              11 F  85     90     90   85    90   80    30   60                              12 F  100    90     65   80    100  100   100  50                              13 F  100    95     100  100   100  100   90   --                              14 F  100    100    100  100   100  100   100  50                              15 F  25     35     15   30    80   25    20    0                              16 F  100    85     70   75    90   90    50   --                              17 F  100    100    100  100   100  100   100  --                              18 F  90     85     85   85    90   95    70   40                              20 F  40     60     10   60    100  100   100  50                              21 F  35     60     10   60    100  100   80   60                              22 F  95     95     35   100   100  100   90   50                              23 F  100    100    40   100   100  100   90   50                              24 F  100    75     100  60    --   100   100  60                              25 F  95     95     90   95    100  100   95   35                              34 F  50     40      0   35    50   70    30   50                              37 F  20     60      0   30    30   50    50   50                              38 F  25     50      0   25    25   50    20   20                              52 F   0     60     50   50    10   50    --   20                              53 F   0     50      0   50    50   50    --   30                              54 F  90     75     60   50    50   80    --   80                              ______________________________________                                          A blank -- indicates the weed was not tested.                            

                  TABLE III-G                                                      ______________________________________                                         Post-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                  Cmpd.                                                                          No.   FT     WG      WO    AMG   VL    MD    YNG                               ______________________________________                                          1 G  100    95      90    90    100   100   80                                 2 G  100    100     100   100   100   100   80                                 3 G  100    100     95    100   100   100   90                                 4 G  100    100     100   100   100   100   90                                 5 G  100    100     100   100   100   100   100                                6 G* 10     80      50    75    40    --     0                                 7 G  70     75      70    90    90    80    80                                 8 G  50     80      70    90    90    80    30                                 9 G  70     80      70    90    90    80    30                                10 G  75     80      70    80    60    50    70                                11 G  70     80      70    80    80    80    80                                12 G  100    75      90    75    80    80    80                                13 G  60     70      70    100   100   100   80                                14 G  20     70      40    60    80    80    70                                15 G  90     70      70    75    80    90    70                                16 G  50     70      80    60    80    90    70                                17 G  90     60      70    65    80    80    80                                18 G  30     50      80    95    95    80    70                                19 G  100    100     95    90    100   100   80                                20 G  10     40       5    70    80    90    70                                21 G  95     90      95    95    100   100   70                                22 G  80     90      90    80    100   100   70                                23 G  90     80      80    80    90    80    30                                24 G   0     30       0    40    80    20     0                                25 G   0     20       0    10    10    20     0                                26 G  80     70      70    80    80    80    70                                27 G  90     90      90    80    80    90    60                                28 G  70     65      50    80    80    80    70                                ______________________________________                                          A blank -- indicates the weed was not tested.                                   *Tested at 0.56 kg/ha.                                                  

PRE-EMERGENCE MULTI-WEED HERBICIDE TEST

Several compounds were evaluated at an application rate of 2 lb/acre (2.24 kg/ha) or 1 lb/acre (1.12 kg/ha) for pre-emergence activity against a larger number of weed species.

The process was generally similar to the pre-emergence herbicide test described above except that only 300 or 150 milligrams of test compound were weighed out and the application arate was 40 gallons per acre.

Redroot pigweed (PW) and curly dock (CD) were eliminated in this test and the following weed species were added:

    ______________________________________                                         Grasses:                                                                              downy brome   Bromus tectorum                                                                              (DB)                                               annual ryegrass                                                                              Lolium multiflorum                                                                           (ARG)                                              rox-orange sorghum                                                                           Sorghum bicolor                                                                              (SHC)                                              hemp sesbania Sesbania exaltata                                                                            (SESB)                                             nightshade    Solanum sp.   (SP)                                               cocklebur     Xattiium sp.  (CB)                                        ______________________________________                                    

The results of the 2.24 kg/ha test are shown in Table IV and the results of the 1.12 kg/ha test are shown in Table VI.

POST-EMERGENCE MULTI-WEED HERBICIDE TEST

Several compounds were evalated at an application rate of 2 lb/acre (2.24 kg/ha) or 1 lb/acre (1.12 kg/ha) for post-emergence activity against the larger number of weed species that are used in the pre-emergent multi-herbicide test.

The process was generally similar to the post-emergence herbicide test described above except that only 300 or 150 milligrams of test compound were weighed out and the application rate was 40 gallons per acre.

The results of the 2.24 kg/ha test are shown in Table V and the results for the 1.12 kg/ha test are shown in Table VII.

                                      TABLE IV-A                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     67 A                                                                               20 90 25   98                                                                                80                                                                               60 90 45  90  45 20  85                                                                               85 15                               68 A                                                                               65 98 98  100                                                                               100                                                                               60 95 100 100 100                                                                               80 100                                                                               95 100                              69 A                                                                               65 100                                                                               70  100                                                                               100                                                                               65 95 100 95  70 65 100                                                                               90 --                               70 A                                                                               98 100                                                                               100 100                                                                               100                                                                               90 98 90  100 90 60 100                                                                               95 80                               71 A                                                                               60 20 100 100                                                                               100                                                                               80 95 35  40  100                                                                               20  90                                                                               100                                                                               40                               72 A                                                                               100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 90  100                                                                               60 100                                                                               100                                                                               20                               83 A                                                                               15 45 25   90                                                                                15                                                                                5 90 45  35  20  0  20                                                                               75 --                               86 A                                                                               20  0 15   60                                                                                60                                                                               20 70 25  45  100                                                                               20 100                                                                               15 35                               87 A                                                                               100                                                                               90 85  100                                                                                85                                                                               25 30 35  85  100                                                                               85 100                                                                               95 40                               __________________________________________________________________________

                                      TABLE VI-A                                   __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 2.24 hg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     86 A                                                                               60 100                                                                               50   90                                                                               50 60 90 70  100 100                                                                                20                                                                               100                                                                               20 --                               87 A                                                                               95 100                                                                               30  100                                                                               80 70 80 95  100 100                                                                               100                                                                               100                                                                               70 --                               __________________________________________________________________________

                                      TABLE V-A                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      82 A                                                                              35 100                                                                               85  100                                                                                65                                                                               60 90 50  90   60                                                                               30  97                                                                               90 40                                85 A                                                                              100                                                                               100                                                                               100 100                                                                               100                                                                               85 100                                                                               20  10  100                                                                               65 100                                                                               100                                                                               30                                92 A                                                                              15 20 45  100                                                                                90                                                                               40 80 95  95  100                                                                               25 100                                                                               90 40                                93 A                                                                              30 75 40  100                                                                               100                                                                               60 90 100 100 100                                                                               35 100                                                                               90 40                                94 A                                                                              30 70 40  100                                                                               100                                                                               30 65 95  85  100                                                                                0 100                                                                               90 30                                95 A                                                                               0  0  0   85                                                                                60                                                                               15 70 65  60  100                                                                               80  90                                                                               10 20                                 96 A                                                                             95 100                                                                               98  100                                                                               100                                                                               70 100                                                                               100 95   90                                                                               80 100                                                                               95 --                                97 A                                                                              100                                                                               100                                                                               98  100                                                                               100                                                                               100                                                                               100                                                                               100 95  100                                                                               70 100                                                                               95 100                               98 A                                                                              10  0  0   0  20                                                                               25 70  0  20   0  0  80                                                                               30 --                                99 A                                                                              15  0  0   75                                                                               25  0 20 30  60   15                                                                               20  30                                                                               25  0                               100 A                                                                               0  0  0   0  0  0 20 10   0   0  0  15                                                                                0 --                               101 A                                                                              100                                                                               98 95  100                                                                               100                                                                               70 98 100 100 100                                                                               20 100                                                                               95 --                               102 A                                                                              25 20 35  100                                                                               100                                                                               45 95 70  100 100                                                                               60 100                                                                               90 --                               103 A                                                                              80 60 45  100                                                                               100                                                                               40 90 65  90  100                                                                                0 100                                                                               95  0                               106 A                                                                              100                                                                               100                                                                               60   40                                                                                95                                                                               35 100                                                                               35  90  100                                                                               70 100                                                                               90 --                               107 A                                                                              100                                                                               100                                                                               100 100                                                                               100                                                                               90 100                                                                               100 100 100                                                                               80 100                                                                               95 30                               108 A                                                                              100                                                                               100                                                                               100 100                                                                               100                                                                               85 100                                                                               100 100 100                                                                               30 100                                                                               95 100                              .sup. 109 A.sup.a                                                                  65 20 85  100                                                                                98                                                                               60 90 30  50  100                                                                               50 100                                                                               90 100                              110 A                                                                               0 60 30  100                                                                                65                                                                               25 65 25  30  100                                                                                0 100                                                                               60  0                               111 A                                                                              100                                                                               100                                                                               100 100                                                                               100                                                                               75 98 100 100 100                                                                               90 100                                                                               -- 70                               112 A                                                                              100                                                                               100                                                                               90  100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               100                                                                               100                                                                               -- --                               113 A                                                                              65 95 40  100                                                                               100                                                                               30 90 70  100 100                                                                                0 100                                                                               -- 30                               114 A                                                                              70 100                                                                               25  100                                                                               100                                                                               40 100                                                                               100 100 100                                                                               30 100                                                                               95 80                               115 A                                                                              100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               45 100                                                                               85 100                              116 A                                                                              25 15 20  100                                                                                65                                                                               35 65 45  50  100                                                                                0 100                                                                               95 10                               119 A                                                                              100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               95 100                                                                               95 90                               120 A                                                                              100                                                                               100                                                                               100 100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               100                                                                               100                                                                               90 100                              122 A                                                                              80 80 45  100                                                                                60                                                                               65 70 100 100 100                                                                               100                                                                               100                                                                               90 100                              123 A                                                                               0 100                                                                               50  100                                                                                85                                                                                0 60 100 90  100                                                                               80 100                                                                               100                                                                               20                               124 A                                                                              25 50 65   90                                                                                65                                                                                0 40 75  80  100                                                                               40  90                                                                               80 60                               __________________________________________________________________________      .sup.a application rate was 0.56 kg/ha.                                  

                                      TABLE VII-A                                  __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      82 A                                                                              60 40 10  98 35 10 30 70  100 100                                                                               100                                                                                90                                                                               45 --                                85 A                                                                              60 60 35  100                                                                               45 60 85 50  100 100                                                                               100                                                                               100                                                                               60 --                                92 A                                                                              70 55 20  80 80 45 100                                                                               95  90   80                                                                               20  95                                                                               70 90                                93 A                                                                              90 90 70  95 95 75 90 98  95   85                                                                               35 100                                                                               60 90                                94 A                                                                              100                                                                               85 45  90 100                                                                               90 100                                                                               100 90   90                                                                               30 100                                                                               60 85                                95 A                                                                              20 60  0  80 70  0 45 60  75   90                                                                                0  65                                                                               20 --                                96 A                                                                              95 100                                                                               90  95 100                                                                               80 95 100 100 100                                                                               70 100                                                                               70 90                                97 A                                                                              100                                                                               100                                                                               95  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               70 100                               98 A                                                                              20  0  0  45 10 50 30 20  65  100                                                                                0  75                                                                               35 80                                99 A                                                                              25 75 15  80 65 10 25 85  100 100                                                                               80 100                                                                               10 --                               100 A                                                                              10 35  0  70 50  5 20 30  70   40                                                                                0 100                                                                               10 100                              101 A                                                                              30 60 25  100                                                                               60 60 80 100 100 100                                                                               30 100                                                                               70 --                               103 A                                                                              90 100                                                                               25  100                                                                               100                                                                               80 100                                                                               100 100 100                                                                               15 100                                                                               40 --                               104 A                                                                              98 98 25  98 100                                                                               15 100                                                                               100 100 100                                                                               60 100                                                                               95 --                               106 A                                                                              75 90 30  90 70 25 100                                                                               100 100 100                                                                               80 100                                                                               75 --                               107 A                                                                              100                                                                               100                                                                               80  90 85 100                                                                               100                                                                               100 100 100                                                                               60 100                                                                               40 --                               108 A                                                                              100                                                                               100                                                                               65  90 60 95 100                                                                               100 100 100                                                                               90 100                                                                               90 --                               .sup. 109 A.sup.a                                                                  90 60 45  90 70 60 98 95  95  100                                                                               98  80                                                                               55 --                               110 A                                                                              50 50 20  100                                                                               50 10 40 100 98   98                                                                               20 100                                                                               35 45                               111 A                                                                              85 90 80  90 70 60 95 100 90  100                                                                               65 100                                                                               80 60                               112 A                                                                              100                                                                               100                                                                               90  100                                                                               100                                                                               95 100                                                                               100 100 100                                                                               45 100                                                                               95 70                               113 A                                                                              70 50 20  90 60 50 80 95  95  100                                                                               60 100                                                                               -- 60                               114 A                                                                              85 100                                                                               15  100                                                                               100                                                                               60 00 100 100 100                                                                               100                                                                               100                                                                               60 --                               115 A                                                                              100                                                                               100                                                                               45  100                                                                               100                                                                               80 100                                                                               100 100 100                                                                               100                                                                               100                                                                               90 --                               116 A                                                                              80 60 25  90 35 40 45 75  90  100                                                                               40  90                                                                               75 60                               119 A                                                                              60 70 30  95 70 20 90 100 100 100                                                                               90 100                                                                               30 85                               120 A                                                                              75 90 60  95 80 45 100                                                                               100 90  100                                                                               65 100                                                                               35 100                              122 A                                                                              60 90 15  100                                                                               30 15 15 100 100 100                                                                               75 100                                                                               45 95                               123 A                                                                               0 100                                                                               35  100                                                                               50 15 85 100 100 100                                                                               100                                                                               100                                                                               70 85                               124 A                                                                              25 100                                                                               35  40 35  0 40 95  100 100                                                                               100                                                                               100                                                                               85 75                               __________________________________________________________________________      .sup.a Application rate was 0.56 kg/ha.                                        A dash mark -- is used in Tables IIVII to indicate that no percent contro      number was available.                                                    

                                      TABLE IV-B                                   __________________________________________________________________________     Pre-Emergence Multi-Weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     14B 80 100                                                                               100 100                                                                               100                                                                               80 95  70  60 100                                                                               40                                                                                85                                                                               100                                                                               10                                21B 85 100                                                                               90  100                                                                               100                                                                               85 100                                                                               100 100 100                                                                               70                                                                               100                                                                               95 100                               24B 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               75                                                                               100                                                                               95 --                                38B 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                                20  10 100                                                                               20                                                                                95                                                                               100                                                                               20                                88B 75 100                                                                               60  100                                                                               100                                                                               70 60  20  40 100                                                                                0                                                                               100                                                                               60 20                                89B 20  60                                                                               30   85                                                                                95                                                                               55 40  15  20  65                                                                                0                                                                               100                                                                               35 50                                90B 60 100                                                                               60  100                                                                               100                                                                               45 30 100 100 100                                                                               15                                                                               100                                                                               50 85                                103B                                                                               95 100                                                                               75  100                                                                               100                                                                               50 85 100 100 100                                                                               80                                                                               100                                                                               80 40                                104B                                                                               60 100                                                                               60  100                                                                               100                                                                               45 30 100 100 100                                                                               15                                                                               100                                                                               50 85                                __________________________________________________________________________      (--) = Specie did not germinate for some reason.                         

                                      TABLE V-B                                    __________________________________________________________________________     Post-Emergence Multi-Weed Herbicide Test                                       Applicaton Rate - 2.24 kg/ha                                                   Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     24B 35  25                                                                               45   60                                                                               65 85 90 100 100 -- 90                                                                               100                                                                               65 --                                88B 60  30                                                                               30   90                                                                               100                                                                               80 100                                                                               100 100 100                                                                               30                                                                               100                                                                               20 100                               89B 50  70                                                                               35   90                                                                               60 35 20 100  90 100                                                                               35                                                                               100                                                                               15 100                               90B 30 100                                                                               40  100                                                                               70 10 25 100 100 100                                                                               30                                                                                90                                                                               50  95                               103B                                                                               95 100                                                                               70  100                                                                               65 75 65 100 100 100                                                                               65                                                                               100                                                                               50 100                               104B                                                                               30 100                                                                               40  100                                                                               70 10 25 100 100 100                                                                               30                                                                                90                                                                               50  95                               __________________________________________________________________________      (--) = Specie did not germinate for some reason.                         

                                      TABLE VI-B                                   __________________________________________________________________________     Pre-Emergence Multi-Weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No.  DB FT ARG WG SHC WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                             __________________________________________________________________________      1B  25  10                                                                               30   85                                                                                55  0 --  55 --  100                                                                               --  75                                                                               75 35                             23B  55  95                                                                               90  100                                                                                95*                                                                               95 95  98 80  -- 10 100                                                                               95 --                             68B  65 100                                                                               60  100                                                                                100*                                                                               6 90 100 90  100                                                                               20 100                                                                               30 40                             69B  70 100                                                                               60  100                                                                                100*                                                                              95 95 100 95  100                                                                                0 100                                                                               85 25                             70B  60 100                                                                               75  100                                                                                100*                                                                              85 100                                                                               100 90  100                                                                               25 100                                                                               90 25                             76B  100                                                                               100                                                                               85  100                                                                                100*                                                                              85 98 100 95  -- 35 100                                                                               95 --                             78B  40  70                                                                               15   95                                                                                75*                                                                               25 80  65 75  --  0 100                                                                               80 --                             79B  100                                                                               100                                                                               100 100                                                                               100 98 100                                                                               100 85  100                                                                               85 100                                                                               95 --                             80B  98 100                                                                               95  100                                                                               100 60 98  99 90  100                                                                               35 100                                                                               85 --                             83B  20 100                                                                               60  100                                                                                100*                                                                              40 90  85 65  100                                                                                0 100                                                                               85 --                             84B   0  90                                                                               25   98                                                                                100*                                                                              30 90  20 35  100                                                                                5 100                                                                               50 --                             85B  80 100                                                                               50  100                                                                               100 60 90 100 90  100                                                                                0 100                                                                               95 --                             86B  60  90                                                                               40  100                                                                               100 60 70  35 60  100                                                                               100                                                                               100                                                                               -- --                             87B   0  90                                                                               15  100                                                                                85 15 70  40 60  100                                                                               40  90                                                                               20 --                             92B  20  40                                                                               10   95                                                                                40 10 60  65 30  100                                                                                0  55                                                                               60  0                             93B  60  95                                                                               20  100                                                                               100 75 100                                                                               100 100 100                                                                                0 100                                                                               40 35                             94B   0  80                                                                               40  100                                                                                95 25 85   80                                                                               40  100                                                                               10  85                                                                               55 10                             95B  98 100                                                                               30  100                                                                               100 40 90 100 100 100                                                                               40 100                                                                               90 30                             96B  100                                                                               100                                                                               75  100                                                                               100 95 100                                                                               100 100 100                                                                               60 100                                                                               85 100                            97B  100                                                                               100                                                                               90  100                                                                               100 95 100                                                                               100 100 100                                                                               60 100                                                                               95 100                            98B  95 100                                                                               100 100                                                                               100 80 100                                                                               100 100 100                                                                               50 100                                                                               100                                                                               60                              99B**                                                                              -- 100                                                                               75  100                                                                                100*                                                                              20 75  50 75   95                                                                                0 -- 85 30                             100B 100                                                                                98                                                                               98  100                                                                               100 90 95 100 75  100                                                                               70 100                                                                               95 40                             102B  0 100                                                                               25  100                                                                                90 75 95  60 60  100                                                                               30 100                                                                               90 --                             __________________________________________________________________________      * = seedling johnsongrass (Sroghum halepense) was substituted for              roxorange sorghum.                                                             ** = Application rate was 0.56 kg/ha                                           (--) = Specie did not germinate for some reason.                         

                                      TABLE VII-B                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No.  DB FT ARG WG SHC WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                             __________________________________________________________________________      1B  45 35 40  90 35  10 --  60 --   75                                                                               --  60                                                                               50 55                             23B  90 100                                                                               80  90  90*                                                                               90 90  80  90  90                                                                               40  70                                                                               25 --                             68B  50 60 40  85  80*                                                                               75 100                                                                                95  90  85                                                                               55 100                                                                               40 --                             69B  70 80 35  90  90*                                                                               80 90  80  85  90                                                                               20  90                                                                               25 --                             70B  100                                                                               90 80  100                                                                               100*                                                                               95 100                                                                               100  95  80                                                                               30  75                                                                               45 90                             76B  100                                                                               100                                                                               98  100                                                                               100*                                                                               100                                                                               100                                                                               100 100 100                                                                               60 100                                                                               40 --                             78B  100                                                                               90 80  85 100*                                                                               70 90 100 100 100                                                                                0  90                                                                               45 --                             79B  80 35 45  70  60*                                                                               70 70  45  98 100                                                                               35  90                                                                               20 --                             80B  60 70 25  90  60*                                                                               60 85  70  90 100                                                                               15 100                                                                               25 100                            85B  95 100                                                                               65  100                                                                               80  90 100                                                                               100 100 100                                                                               25 100                                                                               85 --                             86B  30 60 20  75 50  50 60  50  65 100                                                                               10 100                                                                               20 80                             87B   0  0  0  100                                                                               45  20 30  60  90  80                                                                                0 100                                                                               30 45                             92B  20 80 10  85 15   0 30 100  40 100                                                                                0  60                                                                               60 30                             93B  70 100                                                                               25  100                                                                               100 85 100                                                                               100 100 100                                                                               100                                                                               100                                                                               80 --                             94B  20 70 30  90 80  30 20 100 100 100                                                                               60  30                                                                               30 100                            95B  60 90 15  95 95  25 90 100 100 100                                                                               75 100                                                                               70 100                            96B  50 80  0  90 70  30 100                                                                               100 100 100                                                                               40 100                                                                               20 100                            97B  65 100                                                                               35  100                                                                               75  70 80 100 100 100                                                                               50 100                                                                               50 100                            98B  95 100                                                                               65  95 90  100                                                                               95 100 100  90                                                                               40  80                                                                               60 95                              99B**                                                                              -- 100                                                                               95  90  90*                                                                               90 100                                                                                25  80  40                                                                               100                                                                               -- 35 75                             100B 65 75 60  80 75  60 85 100 100 100                                                                               45 100                                                                               65 60                             102B 30 75 20  80 60   0 40  70 100 100                                                                               30 100                                                                               75 --                             __________________________________________________________________________      * = Seedling johnsongram (Sorghum halepense) was substituted for roxorang      sorghum.                                                                       ** = Application rate was 0.56 kg/ha.                                          (--) = Specie did not germinate for some reason.                         

                                      TABLE IV-C                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     2C  0  100                                                                               0   100                                                                               -- 45 70 65  50  100                                                                               15                                                                               100                                                                               90 --                                __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE V-C                                    __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     2D  0  30 0   100                                                                               -- 0  60 85  95  100                                                                               100                                                                               90 40 --                               __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IV-D                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      7D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 100                               8D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 --                               16D.sup.a                                                                           70                                                                               100                                                                                65 100                                                                               100                                                                               60 98  55 100 100                                                                               90 100                                                                               90 --                               24D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               29D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               30 100                                                                               95  80                              33D  75                                                                                15                                                                                60  90                                                                                90                                                                               20 95 100 100 100                                                                               60 100                                                                               95 100                              53D 100                                                                               100                                                                               100 100                                                                               100                                                                               90 100                                                                               100 100 100                                                                               100                                                                               100                                                                               95 100                              57D 100                                                                               100                                                                                25 100                                                                               100                                                                               30 25 100 100 100                                                                               100                                                                               100                                                                               95 100                              64D.sup.a                                                                          --  0  0   95                                                                                35                                                                                0 15  50  75  75                                                                               25 -- 75  40                              66D.sup.a                                                                          --  0  15  15                                                                                50                                                                               20 50 100 100  75                                                                                0 -- 90 100                              67D.sup.a                                                                          --  0  0  100                                                                               100                                                                                0 25  95  75  50                                                                               25 -- 30  75                              69D.sup.a                                                                          --  30                                                                                0  100                                                                               100                                                                                0 70 100 100 100                                                                               35 -- 95 100                              70D.sup.a                                                                          -- 100                                                                                10 100                                                                               100                                                                               25 65 100 100 100                                                                                0 -- 95 100                              __________________________________________________________________________      (--) = Not tested.                                                             .sup.a = Tested at 0.28 kg/ha.                                           

                                      TABLE V-D                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     34D  90                                                                                85                                                                               30   95                                                                               -- 45  98                                                                                75 100 100                                                                               40 100                                                                               50 --                               35D 100                                                                                85                                                                               70  100                                                                               -- 90 100                                                                               100 100 100                                                                               40 100                                                                               75 --                               40D 100                                                                               100                                                                               20  100                                                                               -- 70 100                                                                                98  98 100                                                                               20 100                                                                               50 --                               41D 100                                                                               100                                                                               80  100                                                                               -- 60 100                                                                               100 100 100                                                                               25 100                                                                               95 --                               42D  50                                                                                60                                                                               40   85                                                                               -- 30 100                                                                               100 100 100                                                                               100                                                                               100                                                                               90 --                               43D  90                                                                                95                                                                               60  100                                                                               -- 30  98                                                                               100  98 100                                                                               45 100                                                                               95 --                               44D  60                                                                               100                                                                               20  100                                                                               -- 60 100                                                                               100  90 100                                                                               20 100                                                                               80 --                               45D  95                                                                               100                                                                               35  100                                                                               -- 60  90                                                                               100 100 100                                                                                0 100                                                                               90 --                               46D 100                                                                               100                                                                               90  100                                                                               -- 95 100                                                                               100 100 100                                                                               40 100                                                                               95 --                               47D 100                                                                               100                                                                               100 100                                                                               -- 98 100                                                                               100  98 100                                                                               30 100                                                                               95 --                               48D 100                                                                               100                                                                               100 100                                                                               -- 100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               100                                                                               --                               49D 100                                                                               100                                                                               100 100                                                                               -- 100                                                                               100                                                                               100 100 100                                                                               90 100                                                                               -- --                               50D 100                                                                               100                                                                               100 100                                                                               100                                                                               85 100                                                                               100 100 100                                                                               90 100                                                                               98 --                               54D 100                                                                               100                                                                               85  100                                                                               100                                                                               15 100                                                                                25 100 100                                                                               65 100                                                                               95 100                              55D  85                                                                               100                                                                               35  100                                                                                98                                                                               15 100                                                                                15 100 100                                                                               65 100                                                                               95 --                               56D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               100                              58D  98                                                                               100                                                                               40   95                                                                                40                                                                               20  95                                                                               100 100 100                                                                               85 100                                                                               100                                                                               95                               59D 100                                                                               100                                                                               100 100                                                                               100                                                                               90 100                                                                               100 100 100                                                                               100                                                                               100                                                                               85 80                               60D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               75 100                                                                               85 80                               __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VI-D                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP                                                                               MD YNS                                                                               CB                                __________________________________________________________________________     61D -- 100                                                                               65  100                                                                               65 20 80 20  40   80                                                                               10                                                                               -- 20  0                                62D -- 50 35   70                                                                               50  0 0   0  25   50                                                                                0                                                                               --  0  0                                63D 100                                                                               100                                                                               100 100                                                                               100                                                                               95 100                                                                               90  95  100                                                                               75                                                                               100                                                                               100                                                                               85                                68D --  0 20   0  0  0 0  60  100 100                                                                               90                                                                               -- 75 75                                71D -- 50 40   50                                                                               75 40 35 75  50   70                                                                                0                                                                               -- 75 75                                72D -- 35 60  100                                                                               85 50 100                                                                               25  65  100                                                                               35                                                                               -- 100                                                                               35                                73D -- 90 70  100                                                                               95 25 0  70  100 100                                                                                0                                                                               -- 50 25                                __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VII-D                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________      7D 100                                                                               100                                                                               100 100                                                                               80  90                                                                                10                                                                                95 100 100                                                                               55 100                                                                               45 100                              16D.sup.a                                                                          100                                                                                85                                                                               35  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               85  70                              24D 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               29D 100                                                                               100                                                                               60  100                                                                               90 100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               33D  90                                                                                98                                                                               85  100                                                                               100                                                                                80                                                                               100                                                                               100 100 100                                                                               90 100                                                                               90 100                              53D 100                                                                               100                                                                               60  100                                                                               100                                                                               100                                                                               100                                                                               100 100 100                                                                               100                                                                               100                                                                               100                                                                               --                               57D  25                                                                                40                                                                               10  100                                                                               10   0                                                                                10                                                                               100  95 100                                                                               35 100                                                                               -- 100                              64D.sup.a                                                                          --  0  0   90                                                                                0  0  85                                                                                40 100  80                                                                               50 -- 35 100                              66D.sup.a                                                                          --  0  0   65                                                                                0  0  70                                                                                75  80  75                                                                                0 -- 25  75                              67D.sup.a                                                                          --  0  0   75                                                                               35  0  40                                                                                70  80  60                                                                                0 --  0 100                              69D.sup.a                                                                          --  0  0   80                                                                               35  0 100                                                                                90 100 100                                                                               40 -- 35 100                              70D.sup.a                                                                          -- 100                                                                                0  100                                                                               70  90                                                                                90                                                                               100 100 100                                                                               30 -- 25 100                              __________________________________________________________________________      (--) = Not tested.                                                             .sup.a = Tested at 0.28 kg/ha.                                           

                                      TABLE VIII-D                                 __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC                                                                               WO BSG                                                                               AMG SESB                                                                               VL SP MD YNS                                                                               CB                               __________________________________________________________________________     34D 90  85                                                                               30   95                                                                               -- 45 98  75 100 100                                                                               40 100                                                                               50 --                               35D 100                                                                                85                                                                               70  100                                                                               -- 90 100                                                                               100 100 100                                                                               40 100                                                                               75 --                               40D 75 100                                                                                5  100                                                                               -- 50 75 100 100 100                                                                               40 100                                                                               30 --                               41D-                                                                               -- -- --  -- -- -- -- --  --  -- -- -- -- --                               42D 40 100                                                                               35  100                                                                               -- 50 80 100 100 100                                                                               80 100                                                                               70 --                               43D 60  70                                                                               20  100                                                                               -- 55 60 100 100 100                                                                               95 100                                                                               70 --                               44D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               45D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               46D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               47D 90 100                                                                               35  100                                                                               -- 75 90 100 100 100                                                                               25 100                                                                               45 --                               48D 80 100                                                                               60  100                                                                               -- 60 80 100 100 100                                                                               85 100                                                                               60 --                               49D -- -- --  -- -- -- -- --  --  -- -- -- -- --                               50D 90  80                                                                               60   95                                                                               80 90 100                                                                               100 100 100                                                                               65 100                                                                               80 --                               54D 35  50                                                                               30  100                                                                               30 15 90 100 100 100                                                                               100                                                                               100                                                                               95 --                               55D 100                                                                               100                                                                               20  100                                                                               90 20 100                                                                                90 100 100                                                                               100                                                                               100                                                                               -- --                               56D 75  90                                                                               75   95                                                                               90 25 100                                                                               100 100 100                                                                               90 100                                                                               90 100                              58D 70 100                                                                               40  100                                                                               95 30 95 100  95 100                                                                               95 100                                                                               95  85                              59D 90 100                                                                               95  100                                                                               100                                                                               50 100                                                                               100 100 100                                                                               95 100                                                                               100                                                                                95                              60D 95 100                                                                               100 100                                                                               100                                                                               75 95 100 100 100                                                                               95 100                                                                               100                                                                               100                              __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IX-D                                   __________________________________________________________________________     Post-Emergence Multi-weed Herbicide Test                                       Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG SHC WO BSG AMG SESB                                                                               VL SP MD YNS CB                            __________________________________________________________________________     61D -- 40 0   50 35  0  40  75  95  100                                                                               0  -- 25  50                            62D -- 35 0   20 0   0  20  35  60  100                                                                               0  -- 0   100                           63D 100                                                                               100                                                                               85  98 85  100                                                                               100 100 100 100                                                                               100                                                                               85 85  95                            68D -- 30 40  85 0   25 60  80  95  100                                                                               95 -- 0   80                            71D -- 50 0   80 65  0  75  100 80  100                                                                               50 -- 25  100                           72D -- 90 70  80 50  50 75  85  100 100                                                                               90 -- 100 100                           73D -- 100                                                                               15  100                                                                               75  75 85  100 100 90 60 -- 80  100                           __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE IV-E                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG AMG SESB                                                                               VL SP MD YNS                                __________________________________________________________________________     17E 95 85 35  100                                                                               85 25 90  100 100 100                                                                               40 100                                                                               95                                 18E 0  0  0   50 20 0  15  60  45  100                                                                               0  100                                                                               --                                 __________________________________________________________________________

                                      TABLE V-E                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG AMG SESB                                                                               VL SP MD YNS                                __________________________________________________________________________      7E 30 70 20  100                                                                               75 0  90  100 95  100                                                                               100                                                                               100                                                                               90                                  8E 95 95 45  100                                                                               98 25 90  100 95  100                                                                               90 100                                                                               90                                  9E 10 70 40  100                                                                               20 0  80  100 85  100                                                                               40 100                                                                               95                                 10E 100                                                                               100                                                                               10  100                                                                               40 0  90  100 100 100                                                                               80 100                                                                               100                                11E 90 100                                                                               90  100                                                                               100                                                                               65 100 100 90  100                                                                               30 100                                                                               65                                 12E 100                                                                               100                                                                               80  100                                                                               100                                                                               85 90  100 100 100                                                                               85 100                                                                               90                                 13E 0  100                                                                               10  100                                                                               100                                                                               80 70  80  90  100                                                                               70 100                                                                               80                                 15E 0  10 0   90 0  0  15  35  30  100                                                                               10 85 75                                 19E 100                                                                               90 0   100                                                                               20 10 40  95  100 100                                                                               100                                                                               100                                                                               65                                 __________________________________________________________________________

                                      TABLE VI-E                                   __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG AMG SESB                                                                               VL SP MD YNS                                __________________________________________________________________________     17E 80 100                                                                               55  95 90 20 60  100 100 100                                                                               75 100                                                                               70                                 18E 0  100                                                                               0   98 20 0  10  70  60  100                                                                               10 100                                                                               45                                 __________________________________________________________________________

                                      TABLE VII-E                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG AMG SESB                                                                               VL SP MD YNS                                __________________________________________________________________________      7E 25 30 0   70 60 20 90  75  95  85 50 100                                                                               35                                  8E 80 80 20  70 70 40 80  50  80  80 60 60 35                                  9E 0  30 0   75 15 25 100 95  100 100                                                                               60 100                                                                               25                                 10E 60 80 20  70 35 25 80  75  90  90 70 100                                                                               45                                 11E 45 100                                                                               20  100                                                                               100                                                                               40 50  100 100 100                                                                               20 100                                                                               35                                 12E 70 60 30  100                                                                               100                                                                               80 98  90  100 100                                                                               70 98 40                                 13E 25 100                                                                               10  100                                                                               100                                                                               85 100 80  100 100                                                                               10 90 25                                 15E 30 65 10  90 50 30 20  85  80  98 30 65 15                                 19E 20 60 10  90 10 15 90  100 100 70 100                                                                               40 85                                 __________________________________________________________________________

                                      TABLE IV-F                                   __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 1.12 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG AMG SESB                                                                               VL SP MD YNS CB                             __________________________________________________________________________     19F 40 35 60  100                                                                               90 30 90  100 100 -- 20 100                                                                               90  --                             26F 25 70 45  95 60 25 85  35  75  -- 20 100                                                                               95  90                             27F 45 65 40  100                                                                               60 25 80  100 85  100                                                                               40 100                                                                               95  35                             28F 80 100                                                                               90  100                                                                               100                                                                               90 100 70  90  100                                                                               30 100                                                                               95  35                             29F 90 45 75  100                                                                               85 40 90  95  90  100                                                                               40 100                                                                               95  --                             30F 90 45 75  100                                                                               90 75 100 100 80  100                                                                               60 100                                                                               95  --                             31F 60 65 75  100                                                                               100                                                                               55 95  100 100 100                                                                               100                                                                               100                                                                               95  --                             32F 90 100                                                                               90  100                                                                               100                                                                               65 85  100 90  100                                                                               95 100                                                                               85  --                             33F 100                                                                               100                                                                               95  100                                                                               100                                                                               95 100 100 100 100                                                                               25 100                                                                               90  --                             35F 90 100                                                                               100 100                                                                               -- 90 90  100 90  100                                                                               10 100                                                                               75  --                             36F 90 35 85  100                                                                               -- 15 80  95  90  100                                                                               50 100                                                                               95  --                             39F 100                                                                               100                                                                               100 100                                                                               100                                                                               95 100 100 100 100                                                                               100                                                                               100                                                                               98  --                             40F 100                                                                               100                                                                               80  100                                                                               100                                                                               70 100 100 100 100                                                                               90 100                                                                               95  --                             41F 100                                                                               100                                                                               100 100                                                                               100                                                                               100                                                                               100 100 100 100                                                                               60 100                                                                               98  --                             42F 60 100                                                                               85  100                                                                               100                                                                               70 95  100 95  100                                                                               10 100                                                                               95  50                             43F 85 100                                                                               25  100                                                                               60 25 98  100 100 100                                                                               100                                                                               100                                                                               90  100                            44F 0  80 10  85 0  0  75  0   30  100                                                                               0  100                                                                               0   10                             45F 25 100                                                                               40  100                                                                               60 0  65  60  60  100                                                                               50 100                                                                               70  0                              50F -- 100                                                                               50  100                                                                               35 35 75      100 100                                                                               --                                       __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE V-F                                    __________________________________________________________________________     Pre-Emergence Multi-weed Herbicide Test                                        Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG AMG SESB                                                                               VL SP MD YNS CB                             __________________________________________________________________________     46F 0  65 35  75 65 0  0   0   35  100                                                                               25 90 80  0                              47F -- 60 35  100                                                                               100                                                                               0  90  100 100 100                                                                               70 -- 100 75                             48F -- 75 20  90 60 0  15  70  35  90 0  -- 20  40                             49F -- 60 10  100                                                                               60 0  50  100 95  100                                                                               40 -- 90  100                            51F -- 40 10  95 40 10 50  65  100 100                                                                               0  -- 95  65                             __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VI-F                                   __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 2.24 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG AMG SESB                                                                               VL SP MD YNS CB                             __________________________________________________________________________     19F 100                                                                               90 65  100                                                                               100                                                                               98 100 100 100 100                                                                               60 100                                                                               70  100                            26F 60 75 60  95 45 50 90  50  90  100                                                                               40 90 60  --                             27F 80 70 65  95 100                                                                               90 100 100 100 100                                                                               85 100                                                                               75  --                             28F 80 100                                                                               75  90 85 80 100 80  80  100                                                                               30 100                                                                               85  85                             29F 85 70 55  90 98 90 100 100 100 100                                                                               35 100                                                                               60  100                            30F 90 80 40  90 85 80 80  70  100 100                                                                               20 100                                                                               40  --                             31F 100                                                                               80 20  100                                                                               100                                                                               100                                                                               100 100 100 100                                                                               100                                                                               100                                                                               85  --                             32F 70 90 60  100                                                                               100                                                                               98 100 100 100 100                                                                               100                                                                               100                                                                               60  --                             33F 95 100                                                                               80  100                                                                               90 100                                                                               100 100 100 100                                                                               70 100                                                                               40  --                             35F 70 90 40  100                                                                               -- 100                                                                               100 100 100 100                                                                               98 100                                                                               30  --                             36F 85 100                                                                               35  100                                                                               -- 20 100 100 100 100                                                                               100                                                                               100                                                                               15  --                             39F 100                                                                               100                                                                               85  100                                                                               100                                                                               100                                                                               100 100 100 100                                                                               100                                                                               100                                                                               90  100                            40F 100                                                                               100                                                                               30  100                                                                               100                                                                               100                                                                               100 100 100 100                                                                               90 100                                                                               75  --                             41F 100                                                                               100                                                                               35  90 70 100                                                                               90  100 100 100                                                                               50 100                                                                               70  --                             42F 45 100                                                                               50  100                                                                               70 55 80  100 100 100                                                                               70 100                                                                               75  100                            43F 25 80 15  98 35 0  20  100 100 100                                                                               100                                                                               100                                                                               60  95                             44F 0  15 0   65 0  0  0   70  100 100                                                                               40 100                                                                               0   100                            45F 0  75 35  70 35 0  60  50  85  100                                                                               50 100                                                                               75  70                             50F -- 40 0   75 45 40 60  100 100 95 30 -- 60  100                            __________________________________________________________________________      (--) = Not tested.                                                       

                                      TABLE VII-F                                  __________________________________________________________________________     Post-Emergence Multi-Weed Herbicidal Activity                                  Application Rate - 0.56 kg/ha                                                  Cmpd.                                                                          No. DB FT ARG WG JG WO BSG AMG SESB                                                                               VL SP MD YNS CB                             __________________________________________________________________________     46F 25 35 20  50 35 35 0   20  75  100                                                                               35 95 --  50                             47F -- 75 25  90 40 25 80  100 100 100                                                                               80 -- 75  100                            48F -- 50 35  80 35 40 0   75  100 85 15 -- 50  75                             49F -- 35 0   75 30 0  20  100 100 100                                                                               80 -- 25  85                             51F -- 35 0   80 35 20 70  50  95  95 25 -- 65  50                             __________________________________________________________________________      (--) = Not Tested.                                                       

The compounds of the present invention and thier salts are useful as herbicides and can be applied in a variety of ways at various concentrations. In practice, the compounds or salts are formulated into herbicidal compositions, by admixture, in herbicidally effective amounts, with the adjuvants and carriers normally employed for facilitating the dispersion of active ingredients for agricultural applications, recognizing the fact that the formulation and mode of application of a toxicant may affect the activity of the materials in a given application. Thus, these active herbicidal compounds or salts can be formulated as granules of relatively large particle size, as wettable powders, as emulsifiable concentrates, as powdery dusts, as flowables, as solutions or as any of several other known types of formulations, depending upon the desired mode of application. These formulations may contain as little as about 0.5% to as much as about 95% or more by weight of active ingredient. A herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from about 0.01 to approximately 10 pounds per acre, preferably from about 0.02 to about 4 pounds per acre.

Wettable powders are in the form of finely divided particles which disperse readily in water or other dispersants. The wettable powder is ultimately applied to the soil either as dry dust or as dispersion in water or other liquid. Typical carriers for wettable powders include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic diluents. Wettable powers normally are prepared to contain about 5% to about 95% of the active ingredient and usually also contain a small amount of wetting, dispersing or emulsifying agent to facilitate wetting and dispersion.

Emulsifiable concentrates are homogeneous liquid compositions which are dispersible in water or other dispersant, and may consist entirely of the active compound or salt with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthal, isophorone and other non-volatile organic solvents. For herbicidal application, these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated. The percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises about 0.5% to 95% of active ingredient by weight of the herbicidal composition.

Granular formulations wherein the toxicant is carried on relatively coarse particles, are usually applied without dilution to the area in which suppression of vegetation is desired. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite and other organic or inorganic materials which absorb or which may be coated with the toxicant. Granular formulations normally are prepared to contain about 0.1% to about 25% of active ingredients which may include surface-active agents such heavy aromatic naphthas, kerosene or other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.

Typical wetting, dispersing or emulsifying agents and adjuvants used in agricultural formulations include, for example, the alkyl and alkyaryl sulfonates and sulfates and their salts; polyhydric alcohols; polyethoxylated alcohols, esters and fatty amines; and other types of surface-active agents, many of which are available in commerce. The surface-active agent, when used, normally comprises from 0.1% to 30% by weight of the herbicidal composition.

Dusts, which are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers for the toxicant, are useful formulations for soil-incorporating application.

Pastes, which are homogeneous suspensions of a finely divided solid toxicant in a liquid carrier such as water or oil, are employed for specific purposes. These formulations normally contain about 5% to about 95% of active ingredient by weight, and may also contain small amounts of a wetting, dispersing or emulsifying agent to facilitate dispersion. For application, the pastes are normally diluted and applied as a spray to the area to be affected.

Other useful formulations for herbicidal applications include simple solutions of the active ingredient in a dispersant in which it is completely soluble at the desired concentration, such as water, acetone, alkylate naphthalenes, xylene and other organic solvents. Pressurized sprays, typically aerosols, wherein the active ingredient is dispersed in finely-divided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freons, may also be used.

The phytotoxic compositions of this invention can be applied to the plants in the conventional manner. Thus, the dust and liquid compositions can be applied to the plant by the use of power-dusters, boom and hand sprayers and spray dusters. The compositions can also be applied from airplanes as a dust or a spray or by rope wick applications because they are effective in very low dosages. In order to modify or control growth of germinating seeds or emerging seedlings, as a typical example, the dust and liquid compositions can be applied to the soil according to conventional methods and can be distributed in the soil to a depth of at least 1/2 inch below the soil surface. It is not necessary that the phytotoxic compositions be mechanically admixed with the soil particles since these compositions can also be applied merely by spraying or sprinkling the surface of the soil. The phytotoxic compositions of this invention can also be applied by addition to irrigation water supplied to the field to be treated. This method of application permits the penetration of the compositions into the soil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations. In the following examples the herbicidal compound can be substituted with the herbicidal salt of the compound.

    __________________________________________________________________________     General Formula with Ranges                                                                         Specific Formula                                          __________________________________________________________________________     EMULSIFIABLE CONCENTRATE FORMULATIONS                                          Herbicidal compound                                                                            5-55 herbicidal compound                                                                          24                                          surfactant(s)   5-25 proprietary blend of oil-                                                                    10                                          solvent(s)     20-90 soluble sulfonates and                                                   100%  polyoxyethylene ethers                                                         polar solvent 27                                                               petroleum hydrocarbon                                                                        39                                                                              100%                                       WETTABLE POWDER FORMULATIONS                                                   herbicidal compound                                                                            3-90 herbicidal compound                                                                          80                                          wetting agent  0.5-2 sodium dialkyl naphthalene                                                                     0.5                                       dispersing agent                                                                              1-8   sulfonate                                                 diluent(s)     8.5-87                                                                               sodium lignosulfonate                                                                         7                                                         100%  attapulgite clay                                                                               12.5                                                                          100%                                       EXTRUDED GRANULAR FORMULATIONS                                                 herbicidal compound                                                                            1-20 herbicidal compound                                                                          10                                          binding agent   0-10 lignin sulfonate                                                                              5                                          diluent(s)     70-99 calcium carbonate                                                                            85                                                         100%                 100%                                       FLOWABLE FORMULATIONS                                                          herbicidal compound                                                                           20-70 herbicidal compound                                                                          45                                          surfactant(s)   1-10 polyoxyethylene ether                                                                        5                                           suspending agent(s)                                                                           0.05-1                                                                               attagel       0.05                                        antifreeze agent                                                                               1-10 propylene glycol                                                                             10                                          antimicrobial agent                                                                            1-10 1,2-benzisothiazoline-3-one                                                                  0.03                                        antifoam agent 0.1-1 silicone defoamer                                                                            0.02                                        solvent         7.95-77.85                                                                          water         39.9                                                       100%                100%                                        __________________________________________________________________________

When salts are used as the active ingredient in the herbicidal compositions of this invention it is recommended to use salts that are agriculturally acceptable.

The phytotoxic compositions of this invention can also contain other additives, for example, fertilizers, other herbicides and other pesticides, used as adjuvant or in combination with any of the above-described adjuvants. Fertilizers useful in combination with the active ingredients include, for example, ammonium nitrate, urea and superphosphate. 

We claim:
 1. Compounds of the formula ##STR97## wherein R³¹ is hydrogen or C₁ -C₄ alkyl;R³² is hydrogen or C₁ -C₄ alkyl ; or R³¹ and R³² together are alkylene having 3 to 6 carbon atoms; R³³ is hydrogen or C₁ -C₄ alkyl; R³⁴ is hydrogen or C₁ -C₄ alkyl; R³⁵ is hydrogen or C₁ -C₄ alkyl; R³⁶ is hydrogen or C₁ -C₄ alkyl; and R³⁷ is hydrogen or 3-C₁ -C₄ alkoxy; and R³⁸ is (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, and their herbicidally effective salts.
 2. The compounds of claim 1 wherein R³¹ is hydrogen or methyl; R³² is hydrogen or methyl; R³³ is hydrogen or methyl; R³⁴ is hydrogen or methyl; R³⁵ is hydrogen or methyl; R³⁶ is hydrogen or methyl; R³⁷ is hydrogen or 3-C₁ -C₄ alkoxy; and R³⁸ is (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5)trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 3. The compounds of claim 2 wherein R³⁷ is hydrogen or 3-methoxy and R³⁸ is hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)-- where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R³⁷ is in the 3-position.
 4. The compounds of claim 2 wherein R³⁷ is hydrogen and R³⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl.
 5. The compound of claim 2 wherein R³¹ is methyl; R³² is methyl, R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is hydrogen.
 6. The compound of claim 2 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is methylthio.
 7. The compound of claim 2 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is trifluoromethyl.
 8. The compound of claim 2 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is trifluoromethyl.
 9. The compound of claim 2 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is ClCH₂ SO₂ --.
 10. The compound of claim 2 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is fluorine.
 11. The compound of claim 2 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is chlorine.
 12. The compound of claim 2 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is CH₃ SO₂ --.
 13. The compound of claim 2 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is n-C₃ H₇ SO₂.
 14. The compound of claim 2 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is CH₃ SO₂.
 15. The compound of claim 2 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is C₂ H₅ SO₂.
 16. The compounds of claim 2 wherein R³⁷ is hydrogen.
 17. The compounds of claim 4 wherein R³¹ and R³² are both hydrogen or both methyl and R³³, R³⁴, R³⁵ and R³⁶ are hydrogen.
 18. The compounds of claim 4 wherein R³⁸ is --SO₂ CH₃.
 19. The compounds of claim 4 wherein R³⁸ is --SO₂ CH₂ Cl.
 20. The compounds of claim 4 wherein R³⁸ is trifluoromethyl.
 21. The compounds of claim 4 wherein R³⁸ is --SO₂ CH₃.
 22. The compounds of claim 4 wherein R³⁸ is chlorine.
 23. The compounds of claim 4 wherein R³⁸ is --SO₂ CH₂ Cl.
 24. The compounds of claim 4 wherein R³⁸ is --SO₂ --n--C₃ H₇.
 25. The compound of claim 2 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen, R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is cyano.
 26. The method of controlling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound having the structural formula ##STR98## wherein R³¹ is hydrogen or C₁ -C₄ alkyl;R³² is hydrogen or C₁ -C₄ alkyl; or R³¹ and R³² together are alkylene having 3 to 6 carbon atoms; R³³ is hydrogen or C₁ -C₄ alkyl; R³⁴ is hydrogen or C₁ -C₄ alkyl; R³⁵ is hydrogen or C₁ -C₄ alkyl; R³⁶ is hydrogen or C₁ -C₄ alkyl; and R³⁷ is hydrogen or 3-C₁ -C₄ alkoxy; and R³⁸ is (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, or its herbicidally effective salts.
 27. The method of claim 26 wherein R³¹ is hydrogen or methyl; R³² is hydrogen or methyl; R³³ is hydrogen or methyl; R³⁴ is hydrogen or methyl; R³⁵ is hydrogen or methyl; R³⁶ is hydrogen or methyl; and R³⁸ is (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C.sub. 1 -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 28. The method of claim 27 wherein R³⁷ is hydrogen or methoxy and R³⁸ is hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluromethoxy; cyano; nitro; trifluromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)-- where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R³⁷ is in the 3-position.
 29. The method of claim 27 wherein R³⁷ is hydrogen and R³⁸ is hydrogen; chlorine; bromine; fluorine; trifluoromethyl; or R² SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 30. The method of claim 27 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is hydrogen.
 31. The method of claim 27 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is methylthio.
 32. The method of claim 27 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is trifluromethyl.
 33. The method of claim 27 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is trifluoromethyl.
 34. The method of claim 27 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is ClCH₂ SO₂ --.
 35. The method of claim 27 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is fluorine.
 36. The method of claim 27 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is chlorine.
 37. The method of claim 27 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is CH₃ SO₂ --.
 38. The method of claim 27 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is n--C₃ H₇ SO₂.
 39. The method of claim 27 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is CH₃ SO₂.
 40. The method of claim 27 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is C₂ H₅ CO₂.
 41. The method of claim 27 wherein R³⁷ is hydrogen.
 42. The method of claim 29 wherein R³¹ and R³² are both hydrogen or both methyl and R³³, R³⁴, R³⁵ and R³⁶ are hydrogen.
 43. The method of claim 42 wherein R³⁸ is --SO₂ CH₃.
 44. The method of claim 42 wherein R³⁸ is --SO₂ CH₂ Cl.
 45. The method of claim 42 wherein R³⁸ is trifluoromethyl.
 46. The method of claim 27 wherein R³¹ as methyl, R³² is methyl; R³² is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is cyano.
 47. An herbicidal composition comprising an herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione compound of the formula ##STR99## wherein R³¹ is hydrogen or C₁ -C₄ alkyl;R³² is hydrogen or C₁ -C₄ alkyl; or R³¹ and R³² together are alkylene having 3 to 6 carbon atoms; R³³ is hydrogen or C₁ -C₄ alkyl; R³⁴ is hydrogen or C₁ -C₄ alkyl; R³⁵ is hydrogen or C₁ -C₄ alkyl; R³⁶ is hydrogen or C₁ -C₄ alkyl; and R³⁷ is hydrogen or 3--C₁ -C₄ alkoxy; and R³⁸ is (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C_(1-C) ₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined, or its herbicidally effective salts and an inert carrier therefor.
 48. The herbicidal composition of claim 47 wherein R³¹ is hydrogen or methyl; R³² is hydrogen or methyl; R³³ is hydrogen or methyl; R³⁴ is hydrogen or methyl; R³⁵ is hydrogen or methyl; R³⁶ is hydrogen or methyl; and R³⁸ is (1) hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5) trifluoromethoxy; (6) cyano; (b 7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b) SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄ alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy; or (12) SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined.
 49. The herbicidal composition of claim 48 wherein R³⁷ is hydrogen.
 50. The herbicidal composition of claim 48 wherein R³⁷ is hydrogen or methoxy and R³⁸ is hydrogen; chlorine; fluorine; bromine; methyl; methoxy; trifluoromethoxy; cyano; nitro; trifluoromethyl; R^(b) SO_(n) -- wherein n is the integer 2 and R^(b) is methyl, chloromethyl, trifluoromethyl, cyanomethyl, ethyl, or n-propyl; --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogen or C₁ -C₄ alkyl; R^(e) C(O)-- where R^(e) is C₁ -C₄ alkyl or C₁ -C₄ alkoxy or SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are as defined and R³⁷ is in the 3-position.
 51. The herbicidal composition of claim 48 wherein R³⁷ is hydrogen and R³⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl.
 52. The herbicidal composition of claim 48 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is hydrogen.
 53. The herbicidal composition of claim 48 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is methylthio.
 54. The herbicidal composition of claim 48 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is trifluoromethyl.
 55. The herbicidal composition of claim 48 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is trifluoromethyl.
 56. The herbicidal composition of claim 48 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is chlorine.
 57. The herbicidal composition of claim 48 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is fluorine.
 58. The herbicidal composition of claim 48 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is chlorine.
 59. The herbicidal composition of claim 48 wherein R³¹ is methyl; R³² is methyl; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is CH₃ SO₂ --.
 60. The herbicidal composition of claim 48 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is n--C₃ H₇ SO₂.
 61. The herbicidal composition of claim 48 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is CH₃ SO₂.
 62. The herbicidal composition of claim 48 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R³⁵ is hydrogen; R³⁶ is hydrogen; R³⁷ is hydrogen; and R³⁸ is C₂ H₅ SO₂.
 63. The herbicidal composition of claim 48 wherein R³¹ is methyl, R³² is methyl, R³³ is hydrogen, R³⁴ is hydrogen, R³⁵ is hydrogen, R³⁶ is hydrogen, R³⁷ is hydrogen and R³⁸ is ClCH₂ SO₂.
 64. The composition of matter of claim 49 wherein R³¹ and R³² are both hydrogen or both methyl and R³³, R³⁴, R³⁵ and R³⁶ are hydrogen.
 65. The composition of matter of claim 64 wherein R³⁸ is --SO₂ CH₃.
 66. The composition of matter of claim 64 wherein R³⁸ is --SO₂ CH₂ Cl.
 67. The composition of matter of claim 64 wherein R³⁸ is trifluoromethyl.
 68. The composition of matter of claim 64 wherein R³⁸ is --SO₂ CH₃.
 69. The herbicidal composition of claim 48 wherein R³¹ is hydrogen; R³² is hydrogen; R³³ is hydrogen; R³⁴ is hydrogen; R hydrogen; R³⁷ is hydrogen; and R³⁸ is cyano. 